CA2796311A1

CA2796311A1 - Fused derivatives as pi3k.delta. inhibitors

Fused derivatives as pi3k.delta. inhibitors Download PDF

Info

Publication number: CA2796311A1
Authority: CA; Canada
Prior art keywords: alkyl; independently selected; halo; compound; alkynyl
Prior art date: 2010-04-14
Legal status : Abandoned

Application number

CA2796311A

Other languages

English (en)

French (fr)

Inventor

Andrew P. Combs

Richard B. Sparks

Eddy W. Yue

Current Assignee

Incyte Corp

Original Assignee

Incyte Corp

Incyte Holdings Corp

Priority date

2010-04-14

Filing date

2011-04-13

Publication date

2011-10-20

2011-04-13 Application filed by Incyte Corp, Incyte Holdings Corp filed Critical Incyte Corp

2011-10-20 Publication of CA2796311A1 publication Critical patent/CA2796311A1/en

Status Abandoned legal-status Critical Current

Links

239000003112 inhibitor Substances 0.000 title description 12
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 65
201000010099 disease Diseases 0.000 claims abstract description 51
108091007960 PI3Ks Proteins 0.000 claims abstract description 43
230000000694 effects Effects 0.000 claims abstract description 21
206010028980 Neoplasm Diseases 0.000 claims abstract description 18
201000011510 cancer Diseases 0.000 claims abstract description 14
150000001875 compounds Chemical class 0.000 claims description 433
125000000217 alkyl group Chemical group 0.000 claims description 331
-1 aminosulfonylamino Chemical group 0.000 claims description 167
125000001072 heteroaryl group Chemical group 0.000 claims description 166
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 145
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 132
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 129
125000003118 aryl group Chemical group 0.000 claims description 124
125000000753 cycloalkyl group Chemical group 0.000 claims description 120
125000001424 substituent group Chemical group 0.000 claims description 111
238000000034 method Methods 0.000 claims description 103
150000003839 salts Chemical class 0.000 claims description 102
239000000203 mixture Substances 0.000 claims description 96
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 92
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 84
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 83
125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 82
125000003710 aryl alkyl group Chemical group 0.000 claims description 80
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 80
125000006598 aminocarbonylamino group Chemical group 0.000 claims description 78
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 78
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 73
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 41
125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 41
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 41
102000038030 PI3Ks Human genes 0.000 claims description 40
125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims description 39
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 39
125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 37
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 26
229910052757 nitrogen Inorganic materials 0.000 claims description 26
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 25
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 25
108091000080 Phosphotransferase Proteins 0.000 claims description 25
125000002619 bicyclic group Chemical group 0.000 claims description 25
102000020233 phosphotransferase Human genes 0.000 claims description 25
125000004433 nitrogen atom Chemical group N* 0.000 claims description 24
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 23
229960000643 adenine Drugs 0.000 claims description 23
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 22
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 21
125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims description 20
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 20
125000005311 halosulfanyl group Chemical group 0.000 claims description 18
125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 15
125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 15
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
229910052760 oxygen Inorganic materials 0.000 claims description 14
206010039073 rheumatoid arthritis Diseases 0.000 claims description 14
229910052717 sulfur Inorganic materials 0.000 claims description 13
125000003342 alkenyl group Chemical group 0.000 claims description 12
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical group N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 11
125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
125000002947 alkylene group Chemical group 0.000 claims description 8
125000004438 haloalkoxy group Chemical group 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
206010061218 Inflammation Diseases 0.000 claims description 7
230000014509 gene expression Effects 0.000 claims description 7
230000004054 inflammatory process Effects 0.000 claims description 7
229940043355 kinase inhibitor Drugs 0.000 claims description 7
230000035772 mutation Effects 0.000 claims description 7
239000003757 phosphotransferase inhibitor Substances 0.000 claims description 7
229940124639 Selective inhibitor Drugs 0.000 claims description 6
201000001320 Atherosclerosis Diseases 0.000 claims description 5
208000019693 Lung disease Diseases 0.000 claims description 5
208000006673 asthma Diseases 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 4
208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 4
206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 4
208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims description 4
208000010833 Chronic myeloid leukaemia Diseases 0.000 claims description 4
208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims description 4
208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 4
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208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 4
230000002159 abnormal effect Effects 0.000 claims description 4
206010069351 acute lung injury Diseases 0.000 claims description 4
208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 4
201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 4
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210000004556 brain Anatomy 0.000 claims description 4
210000000481 breast Anatomy 0.000 claims description 4
210000001072 colon Anatomy 0.000 claims description 4
230000002489 hematologic effect Effects 0.000 claims description 4
230000002401 inhibitory effect Effects 0.000 claims description 4
GZUGQAQHLGBSQE-UHFFFAOYSA-N n-[1-[4-chloro-7-(3-fluorophenyl)pyrazolo[1,5-a]pyridin-6-yl]ethyl]-7h-purin-6-amine Chemical compound N=1C=NC=2NC=NC=2C=1NC(C)C=1C=C(Cl)C2=CC=NN2C=1C1=CC=CC(F)=C1 GZUGQAQHLGBSQE-UHFFFAOYSA-N 0.000 claims description 4
CFAVKYVGEDEJEB-UHFFFAOYSA-N n-[1-[4-chloro-7-(3-methoxyphenyl)pyrazolo[1,5-a]pyridin-6-yl]ethyl]-7h-purin-6-amine Chemical compound COC1=CC=CC(C=2N3N=CC=C3C(Cl)=CC=2C(C)NC=2C=3N=CNC=3N=CN=2)=C1 CFAVKYVGEDEJEB-UHFFFAOYSA-N 0.000 claims description 4
UQIJGKNUPVXWKK-UHFFFAOYSA-N n-[1-[4-fluoro-7-(3-fluorophenyl)pyrazolo[1,5-a]pyridin-6-yl]ethyl]-7h-purin-6-amine Chemical compound N=1C=NC=2NC=NC=2C=1NC(C)C=1C=C(F)C2=CC=NN2C=1C1=CC=CC(F)=C1 UQIJGKNUPVXWKK-UHFFFAOYSA-N 0.000 claims description 4
CDQOQNIIEOOBOW-PIJUOVFKSA-N n-[1-[8-chloro-5-[(3r)-3-methoxypyrrolidin-1-yl]imidazo[1,5-a]pyridin-6-yl]ethyl]-7h-purin-6-amine Chemical compound C1[C@H](OC)CCN1C1=C(C(C)NC=2C=3N=CNC=3N=CN=2)C=C(Cl)C2=CN=CN12 CDQOQNIIEOOBOW-PIJUOVFKSA-N 0.000 claims description 4
210000002307 prostate Anatomy 0.000 claims description 4
FXETZJDMXLUXQA-UHFFFAOYSA-N 1-[4-[8-chloro-6-[1-(7h-purin-6-ylamino)ethyl]imidazo[1,5-a]pyridin-5-yl]piperazin-1-yl]-2-methoxyethanone Chemical compound C1CN(C(=O)COC)CCN1C1=C(C(C)NC=2C=3N=CNC=3N=CN=2)C=C(Cl)C2=CN=CN12 FXETZJDMXLUXQA-UHFFFAOYSA-N 0.000 claims description 3
YUQWJNUYVCEZSB-UHFFFAOYSA-N 3-[4-[8-chloro-6-[1-(7h-purin-6-ylamino)ethyl]imidazo[1,5-a]pyridin-5-yl]piperazin-1-yl]-3-oxopropanenitrile Chemical compound N=1C=NC=2NC=NC=2C=1NC(C)C=1C=C(Cl)C2=CN=CN2C=1N1CCN(C(=O)CC#N)CC1 YUQWJNUYVCEZSB-UHFFFAOYSA-N 0.000 claims description 3
206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 3
208000020084 Bone disease Diseases 0.000 claims description 3
206010012689 Diabetic retinopathy Diseases 0.000 claims description 3
206010018364 Glomerulonephritis Diseases 0.000 claims description 3
206010020751 Hypersensitivity Diseases 0.000 claims description 3
208000022559 Inflammatory bowel disease Diseases 0.000 claims description 3
206010033645 Pancreatitis Diseases 0.000 claims description 3
208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 3
UHHXBAZFSGNWTO-UHFFFAOYSA-N [4-[8-chloro-6-[1-(7h-purin-6-ylamino)ethyl]imidazo[1,5-a]pyridin-5-yl]piperazin-1-yl]-(1-methylpyrazol-4-yl)methanone Chemical compound N=1C=NC=2NC=NC=2C=1NC(C)C=1C=C(Cl)C2=CN=CN2C=1N(CC1)CCN1C(=O)C=1C=NN(C)C=1 UHHXBAZFSGNWTO-UHFFFAOYSA-N 0.000 claims description 3
208000026935 allergic disease Diseases 0.000 claims description 3
230000007815 allergy Effects 0.000 claims description 3
230000033115 angiogenesis Effects 0.000 claims description 3
230000002357 endometrial effect Effects 0.000 claims description 3
208000017169 kidney disease Diseases 0.000 claims description 3
201000006417 multiple sclerosis Diseases 0.000 claims description 3
UKWRDQJWNNAIRI-UHFFFAOYSA-N n-[1-(8-chloro-5-piperazin-1-ylimidazo[1,5-a]pyridin-6-yl)ethyl]-7h-purin-6-amine;dihydrochloride Chemical compound Cl.Cl.N=1C=NC=2NC=NC=2C=1NC(C)C=1C=C(Cl)C2=CN=CN2C=1N1CCNCC1 UKWRDQJWNNAIRI-UHFFFAOYSA-N 0.000 claims description 3
LHQLJYPJXGVDOQ-UHFFFAOYSA-N n-[1-[8-chloro-5-(3-fluorophenyl)-3-methylimidazo[1,5-a]pyridin-6-yl]ethyl]-7h-purin-6-amine Chemical compound N=1C=NC=2NC=NC=2C=1NC(C)C=1C=C(Cl)C2=CN=C(C)N2C=1C1=CC=CC(F)=C1 LHQLJYPJXGVDOQ-UHFFFAOYSA-N 0.000 claims description 3
LUPDJKWERKORSV-UHFFFAOYSA-N n-[1-[8-chloro-5-(3-fluorophenyl)imidazo[1,2-a]pyridin-6-yl]ethyl]-7h-purin-6-amine Chemical compound N=1C=NC=2NC=NC=2C=1NC(C)C=1C=C(Cl)C2=NC=CN2C=1C1=CC=CC(F)=C1 LUPDJKWERKORSV-UHFFFAOYSA-N 0.000 claims description 3
VGHYNTJVONZAKN-UHFFFAOYSA-N n-[1-[8-chloro-5-(3-fluorophenyl)imidazo[1,5-a]pyridin-6-yl]ethyl]-7h-purin-6-amine Chemical compound N=1C=NC=2NC=NC=2C=1NC(C)C=1C=C(Cl)C2=CN=CN2C=1C1=CC=CC(F)=C1 VGHYNTJVONZAKN-UHFFFAOYSA-N 0.000 claims description 3
NQIBFFFFIOEFJA-UHFFFAOYSA-N n-[1-[8-chloro-5-(3-fluorophenyl)imidazo[1,5-a]pyridin-6-yl]propyl]-7h-purin-6-amine Chemical compound N=1C=NC=2NC=NC=2C=1NC(CC)C=1C=C(Cl)C2=CN=CN2C=1C1=CC=CC(F)=C1 NQIBFFFFIOEFJA-UHFFFAOYSA-N 0.000 claims description 3
HQRQCFZBNLVPTM-UHFFFAOYSA-N n-[1-[8-chloro-5-(4-methylsulfonylpiperazin-1-yl)imidazo[1,5-a]pyridin-6-yl]ethyl]-7h-purin-6-amine Chemical compound N=1C=NC=2NC=NC=2C=1NC(C)C=1C=C(Cl)C2=CN=CN2C=1N1CCN(S(C)(=O)=O)CC1 HQRQCFZBNLVPTM-UHFFFAOYSA-N 0.000 claims description 3
OGUFVMQVKFNMBJ-UHFFFAOYSA-N n-[1-[8-chloro-5-[4-(2-methoxyethyl)piperazin-1-yl]imidazo[1,5-a]pyridin-6-yl]ethyl]-7h-purin-6-amine Chemical compound C1CN(CCOC)CCN1C1=C(C(C)NC=2C=3N=CNC=3N=CN=2)C=C(Cl)C2=CN=CN12 OGUFVMQVKFNMBJ-UHFFFAOYSA-N 0.000 claims description 3
IJKSLQLUFPKCOZ-UHFFFAOYSA-N n-[1-[8-chloro-5-[4-(4,4,4-trifluorobutyl)piperazin-1-yl]imidazo[1,5-a]pyridin-6-yl]ethyl]-7h-purin-6-amine Chemical compound N=1C=NC=2NC=NC=2C=1NC(C)C=1C=C(Cl)C2=CN=CN2C=1N1CCN(CCCC(F)(F)F)CC1 IJKSLQLUFPKCOZ-UHFFFAOYSA-N 0.000 claims description 3
JJXSDNRFINYKND-UHFFFAOYSA-N n-[1-[8-chloro-5-[4-(oxolan-2-ylmethyl)piperazin-1-yl]imidazo[1,5-a]pyridin-6-yl]ethyl]-7h-purin-6-amine Chemical compound N=1C=NC=2NC=NC=2C=1NC(C)C=1C=C(Cl)C2=CN=CN2C=1N(CC1)CCN1CC1CCCO1 JJXSDNRFINYKND-UHFFFAOYSA-N 0.000 claims description 3
RIBMQVNDPYOYQF-UHFFFAOYSA-N n-[1-[8-fluoro-5-(3-fluorophenyl)imidazo[1,5-a]pyridin-6-yl]ethyl]-7h-purin-6-amine Chemical compound N=1C=NC=2NC=NC=2C=1NC(C)C=1C=C(F)C2=CN=CN2C=1C1=CC=CC(F)=C1 RIBMQVNDPYOYQF-UHFFFAOYSA-N 0.000 claims description 3
208000037803 restenosis Diseases 0.000 claims description 3
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FZHRJQUWRXGICW-RRKGBCIJSA-N (3r)-1-[8-chloro-6-[1-(7h-purin-6-ylamino)ethyl]imidazo[1,5-a]pyridin-5-yl]pyrrolidin-3-ol Chemical compound N=1C=NC=2NC=NC=2C=1NC(C)C=1C=C(Cl)C2=CN=CN2C=1N1CC[C@@H](O)C1 FZHRJQUWRXGICW-RRKGBCIJSA-N 0.000 claims description 2
FZHRJQUWRXGICW-DTIOYNMSSA-N (3s)-1-[8-chloro-6-[1-(7h-purin-6-ylamino)ethyl]imidazo[1,5-a]pyridin-5-yl]pyrrolidin-3-ol Chemical compound N=1C=NC=2NC=NC=2C=1NC(C)C=1C=C(Cl)C2=CN=CN2C=1N1CC[C@H](O)C1 FZHRJQUWRXGICW-DTIOYNMSSA-N 0.000 claims description 2
SIOLKYABFJVNTA-UHFFFAOYSA-N 1-[4-[8-bromo-6-[1-(7h-purin-6-ylamino)ethyl]imidazo[1,5-a]pyridin-5-yl]piperazin-1-yl]ethanone Chemical compound N=1C=NC=2NC=NC=2C=1NC(C)C=1C=C(Br)C2=CN=CN2C=1N1CCN(C(C)=O)CC1 SIOLKYABFJVNTA-UHFFFAOYSA-N 0.000 claims description 2
FLROBJGGWVTIMN-UHFFFAOYSA-N 1-[4-[8-chloro-6-[1-(7h-purin-6-ylamino)ethyl]imidazo[1,5-a]pyridin-5-yl]piperazin-1-yl]ethanone Chemical compound N=1C=NC=2NC=NC=2C=1NC(C)C=1C=C(Cl)C2=CN=CN2C=1N1CCN(C(C)=O)CC1 FLROBJGGWVTIMN-UHFFFAOYSA-N 0.000 claims description 2
AYFDDFRGNJJJJC-UHFFFAOYSA-N 2-[4-[8-chloro-6-[1-(7h-purin-6-ylamino)ethyl]imidazo[1,5-a]pyridin-5-yl]piperazin-1-yl]acetonitrile Chemical compound N=1C=NC=2NC=NC=2C=1NC(C)C=1C=C(Cl)C2=CN=CN2C=1N1CCN(CC#N)CC1 AYFDDFRGNJJJJC-UHFFFAOYSA-N 0.000 claims description 2
208000003950 B-cell lymphoma Diseases 0.000 claims description 2
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NQDGJMGIJQOBLK-UHFFFAOYSA-N [4-[8-chloro-6-[1-(7h-purin-6-ylamino)ethyl]imidazo[1,5-a]pyridin-5-yl]piperazin-1-yl]-cyclopropylmethanone Chemical compound N=1C=NC=2NC=NC=2C=1NC(C)C=1C=C(Cl)C2=CN=CN2C=1N(CC1)CCN1C(=O)C1CC1 NQDGJMGIJQOBLK-UHFFFAOYSA-N 0.000 claims description 2
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NTQXNZHLTKMWFF-UHFFFAOYSA-N n-[1-[8-chloro-5-(3,5-difluorophenyl)-3-methylimidazo[1,5-a]pyridin-6-yl]ethyl]-7h-purin-6-amine Chemical compound N=1C=NC=2NC=NC=2C=1NC(C)C=1C=C(Cl)C2=CN=C(C)N2C=1C1=CC(F)=CC(F)=C1 NTQXNZHLTKMWFF-UHFFFAOYSA-N 0.000 claims description 2
LHUHZJMOULYYAE-UHFFFAOYSA-N n-[1-[8-chloro-5-(3,5-difluorophenyl)-3-methylimidazo[1,5-a]pyridin-6-yl]propyl]-7h-purin-6-amine Chemical compound N=1C=NC=2NC=NC=2C=1NC(CC)C=1C=C(Cl)C2=CN=C(C)N2C=1C1=CC(F)=CC(F)=C1 LHUHZJMOULYYAE-UHFFFAOYSA-N 0.000 claims description 2
YTCWOBVMJRSDQP-UHFFFAOYSA-N n-[1-[8-chloro-5-(4-cyclobutylpiperazin-1-yl)imidazo[1,5-a]pyridin-6-yl]ethyl]-7h-purin-6-amine Chemical compound N=1C=NC=2NC=NC=2C=1NC(C)C=1C=C(Cl)C2=CN=CN2C=1N(CC1)CCN1C1CCC1 YTCWOBVMJRSDQP-UHFFFAOYSA-N 0.000 claims description 2
LFHGSYSOXLSSNU-UHFFFAOYSA-N n-[1-[8-chloro-5-(diethylamino)-3-methylimidazo[1,5-a]pyridin-6-yl]ethyl]-7h-purin-6-amine Chemical compound C1=C(Cl)C2=CN=C(C)N2C(N(CC)CC)=C1C(C)NC1=NC=NC2=C1N=CN2 LFHGSYSOXLSSNU-UHFFFAOYSA-N 0.000 claims description 2
CDQOQNIIEOOBOW-KIYNQFGBSA-N n-[1-[8-chloro-5-[(3s)-3-methoxypyrrolidin-1-yl]imidazo[1,5-a]pyridin-6-yl]ethyl]-7h-purin-6-amine Chemical compound C1[C@@H](OC)CCN1C1=C(C(C)NC=2C=3N=CNC=3N=CN=2)C=C(Cl)C2=CN=CN12 CDQOQNIIEOOBOW-KIYNQFGBSA-N 0.000 claims description 2
QUAJSUWKTXHJLC-UHFFFAOYSA-N n-[1-[8-chloro-5-[4-(cyclopropylmethyl)piperazin-1-yl]imidazo[1,5-a]pyridin-6-yl]ethyl]-7h-purin-6-amine Chemical compound N=1C=NC=2NC=NC=2C=1NC(C)C=1C=C(Cl)C2=CN=CN2C=1N(CC1)CCN1CC1CC1 QUAJSUWKTXHJLC-UHFFFAOYSA-N 0.000 claims description 2
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GFECVMGMJNFQMQ-UHFFFAOYSA-N tert-butyl 4-[8-chloro-6-[1-(7h-purin-6-ylamino)ethyl]imidazo[1,5-a]pyridin-5-yl]piperazine-1-carboxylate Chemical compound N=1C=NC=2NC=NC=2C=1NC(C)C=1C=C(Cl)C2=CN=CN2C=1N1CCN(C(=O)OC(C)(C)C)CC1 GFECVMGMJNFQMQ-UHFFFAOYSA-N 0.000 claims description 2
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125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 157
125000001475 halogen functional group Chemical group 0.000 claims 72
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239000007858 starting material Substances 0.000 description 59
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
239000000243 solution Substances 0.000 description 56
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 53
125000004432 carbon atom Chemical group C* 0.000 description 51
238000006243 chemical reaction Methods 0.000 description 43
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
125000001188 haloalkyl group Chemical group 0.000 description 39
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 37
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 36
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LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
239000000047 product Substances 0.000 description 31
238000000746 purification Methods 0.000 description 29
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
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239000012267 brine Substances 0.000 description 23
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