MXPA04007516A - Derivados de dihidrobenzodiazepin-2-ona para tratamiento de enfermedades neurologicas. - Google Patents

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Publication number

MXPA04007516A

MXPA04007516A MXPA04007516A MXPA04007516A MXPA04007516A MX PA04007516 A MXPA04007516 A MX PA04007516A MX PA04007516 A MXPA04007516 A MX PA04007516A MX PA04007516 A MXPA04007516 A MX PA04007516A MX PA04007516 A MXPA04007516 A MX PA04007516A

Authority

MX

Mexico

Prior art keywords

phenyl

pyridin

methyl

mmol

trifluoromethyl

Prior art date

2002-02-06

Links

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• 208000012902 Nervous system disease Diseases 0.000 title claims abstract description 7
• 208000025966 Neurological disease Diseases 0.000 title claims abstract description 7
• 238000000034 method Methods 0.000 claims abstract description 714
• 150000001875 compounds Chemical class 0.000 claims abstract description 606
• 238000002360 preparation method Methods 0.000 claims abstract description 22
• 239000003814 drug Substances 0.000 claims abstract description 13
• 230000001154 acute effect Effects 0.000 claims abstract description 8
• 230000008569 process Effects 0.000 claims abstract description 7
• ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims abstract description 7
• 230000001684 chronic effect Effects 0.000 claims abstract description 6
• 230000002265 prevention Effects 0.000 claims abstract description 6
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 5
• -1 -NR'R " Chemical group 0.000 claims description 679
• 239000002253 acid Substances 0.000 claims description 153
• 125000000217 alkyl group Chemical group 0.000 claims description 73
• AZIZBYRGIGKTLW-UHFFFAOYSA-N 1,4-diazepin-2-one Chemical compound O=C1C=NC=CC=N1 AZIZBYRGIGKTLW-UHFFFAOYSA-N 0.000 claims description 54
• 125000003545 alkoxy group Chemical group 0.000 claims description 51
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 51
• 125000003282 alkyl amino group Chemical group 0.000 claims description 34
• 239000001257 hydrogen Substances 0.000 claims description 32
• 229910052739 hydrogen Inorganic materials 0.000 claims description 32
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 32
• 229910052736 halogen Inorganic materials 0.000 claims description 30
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 28
• 150000003839 salts Chemical class 0.000 claims description 22
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 21
• 125000001424 substituent group Chemical group 0.000 claims description 19
• 125000001153 fluoro group Chemical group F* 0.000 claims description 18
• 150000002367 halogens Chemical group 0.000 claims description 18
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
• 125000004001 thioalkyl group Chemical group 0.000 claims description 12
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 10
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 10
• 229910052731 fluorine Inorganic materials 0.000 claims description 10
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
• 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 8
• 238000004519 manufacturing process Methods 0.000 claims description 8
• 125000004076 pyridyl group Chemical group 0.000 claims description 8
• 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
• 239000011737 fluorine Substances 0.000 claims description 6
• 208000028017 Psychotic disease Diseases 0.000 claims description 5
• 125000003277 amino group Chemical group 0.000 claims description 5
• 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 5
• 238000007363 ring formation reaction Methods 0.000 claims description 5
• 208000024827 Alzheimer disease Diseases 0.000 claims description 4
• 208000026139 Memory disease Diseases 0.000 claims description 4
• 125000003342 alkenyl group Chemical group 0.000 claims description 4
• 238000010511 deprotection reaction Methods 0.000 claims description 4
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
• 125000003709 fluoroalkyl group Chemical group 0.000 claims description 4
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
• 201000000980 schizophrenia Diseases 0.000 claims description 4
• YJNILYRQRSSTPP-UHFFFAOYSA-N 4-(3-pyridin-3-ylphenyl)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC2=CC(C(F)(F)F)=CC=C2N=C1C(C=1)=CC=CC=1C1=CC=CN=C1 YJNILYRQRSSTPP-UHFFFAOYSA-N 0.000 claims description 3
• YQKASQGOPRPMLH-UHFFFAOYSA-N 7-(dimethylamino)-4-(3-pyridin-4-ylphenyl)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(N(C)C)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=NC=C1 YQKASQGOPRPMLH-UHFFFAOYSA-N 0.000 claims description 3
• ZTMGYWMZJBHXBD-UHFFFAOYSA-N 7-methyl-4-[3-(2-methylpyridin-4-yl)phenyl]-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(=C(C)C=C3N=2)C(F)(F)F)=C1 ZTMGYWMZJBHXBD-UHFFFAOYSA-N 0.000 claims description 3
• 208000010877 cognitive disease Diseases 0.000 claims description 3
• 125000000623 heterocyclic group Chemical group 0.000 claims description 3
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
• GGCAJGPNBPIIQA-UHFFFAOYSA-N 4-[3-(2,6-dimethylpyridin-4-yl)phenyl]-7-ethoxy-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(OCC)=CC=2N=C1C(C=1)=CC=CC=1C1=CC(C)=NC(C)=C1 GGCAJGPNBPIIQA-UHFFFAOYSA-N 0.000 claims description 2
• UVNQIBJKZJJBQK-UHFFFAOYSA-N 4-[3-(2,6-dimethylpyridin-4-yl)phenyl]-7-ethyl-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(CC)=CC=2N=C1C(C=1)=CC=CC=1C1=CC(C)=NC(C)=C1 UVNQIBJKZJJBQK-UHFFFAOYSA-N 0.000 claims description 2
• AFSJGBXRHLXBHV-UHFFFAOYSA-N 4-[3-(2-ethyl-6-methylpyridin-4-yl)phenyl]-7-methyl-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound CC1=NC(CC)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(=C(C)C=C3N=2)C(F)(F)F)=C1 AFSJGBXRHLXBHV-UHFFFAOYSA-N 0.000 claims description 2
• XRLZWRIHQVVACZ-UHFFFAOYSA-N 4-[3-(2-methylpyridin-4-yl)phenyl]-8-(trifluoromethoxy)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(OC(F)(F)F)=CC=C3N=2)=C1 XRLZWRIHQVVACZ-UHFFFAOYSA-N 0.000 claims description 2
• DFWDFOZNVALGES-UHFFFAOYSA-N 4-[3-(2-methylpyridin-4-yl)phenyl]-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(=CC=C3N=2)C(F)(F)F)=C1 DFWDFOZNVALGES-UHFFFAOYSA-N 0.000 claims description 2
• PBXFRAFAGCEVSF-UHFFFAOYSA-N 4-[3-(6-cyclopropylpyridin-3-yl)phenyl]-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC2=CC(C(F)(F)F)=CC=C2N=C1C(C=1)=CC=CC=1C(C=N1)=CC=C1C1CC1 PBXFRAFAGCEVSF-UHFFFAOYSA-N 0.000 claims description 2
• BAXARIOGPJRTLH-UHFFFAOYSA-N 7-(cyclopropylmethoxy)-4-[3-(2-methylpyridin-4-yl)phenyl]-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(=C(OCC4CC4)C=C3N=2)C(F)(F)F)=C1 BAXARIOGPJRTLH-UHFFFAOYSA-N 0.000 claims description 2
• CCOJJDFNFUBNKN-UHFFFAOYSA-N 7-(dimethylamino)-4-[3-(2-methylpyridin-4-yl)phenyl]-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(N(C)C)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=NC(C)=C1 CCOJJDFNFUBNKN-UHFFFAOYSA-N 0.000 claims description 2
• QFBDRSIFOKYSDY-UHFFFAOYSA-N 7-ethoxy-4-(3-pyridin-4-ylphenyl)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(OCC)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=NC=C1 QFBDRSIFOKYSDY-UHFFFAOYSA-N 0.000 claims description 2
• QCDLBZFFNJYTAV-UHFFFAOYSA-N 7-ethyl-4-[3-(2-methylpyridin-4-yl)phenyl]-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(CC)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=NC(C)=C1 QCDLBZFFNJYTAV-UHFFFAOYSA-N 0.000 claims description 2
• OQTSPIQICMTNOL-UHFFFAOYSA-N 7-methyl-4-(3-pyridazin-4-ylphenyl)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(C)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=NN=C1 OQTSPIQICMTNOL-UHFFFAOYSA-N 0.000 claims description 2
• WLGXHFREMLNUDH-UHFFFAOYSA-N 7-methyl-4-(3-pyridin-3-ylphenyl)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(C)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=CN=C1 WLGXHFREMLNUDH-UHFFFAOYSA-N 0.000 claims description 2
• ZYGZDPKEZBLAHD-UHFFFAOYSA-N 7-methyl-4-(3-pyridin-4-ylphenyl)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(C)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=NC=C1 ZYGZDPKEZBLAHD-UHFFFAOYSA-N 0.000 claims description 2
• IWRBJKPPNKZIAC-UHFFFAOYSA-N 7-methyl-4-[2-(2-methylpyridin-4-yl)pyridin-4-yl]-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=NC(C)=CC(C=2N=CC=C(C=2)C=2CC(=O)NC3=CC(=C(C)C=C3N=2)C(F)(F)F)=C1 IWRBJKPPNKZIAC-UHFFFAOYSA-N 0.000 claims description 2
• NZWUYDARLBVUAZ-UHFFFAOYSA-N 8-(2-fluorophenyl)-4-(3-pyridin-3-ylphenyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound FC1=CC=CC=C1C1=CC=C(N=C(CC(=O)N2)C=3C=C(C=CC=3)C=3C=NC=CC=3)C2=C1 NZWUYDARLBVUAZ-UHFFFAOYSA-N 0.000 claims description 2
• DEOUQGPUEWWMNC-UHFFFAOYSA-N 8-(2-fluorophenyl)-4-(3-pyridin-4-ylphenyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound FC1=CC=CC=C1C1=CC=C(N=C(CC(=O)N2)C=3C=C(C=CC=3)C=3C=CN=CC=3)C2=C1 DEOUQGPUEWWMNC-UHFFFAOYSA-N 0.000 claims description 2
• PQMAJJWGJPOQQE-UHFFFAOYSA-N 8-chloro-4-(3-pyridin-3-ylphenyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC2=CC(Cl)=CC=C2N=C1C(C=1)=CC=CC=1C1=CC=CN=C1 PQMAJJWGJPOQQE-UHFFFAOYSA-N 0.000 claims description 2
• QWFYXUVFCJKYON-UHFFFAOYSA-N 8-chloro-4-(3-pyridin-4-ylphenyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC2=CC(Cl)=CC=C2N=C1C(C=1)=CC=CC=1C1=CC=NC=C1 QWFYXUVFCJKYON-UHFFFAOYSA-N 0.000 claims description 2
• JLXAVOQTRVUYKG-UHFFFAOYSA-N 8-chloro-4-[3-(2-methylpyridin-3-yl)phenyl]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound CC1=NC=CC=C1C1=CC=CC(C=2CC(=O)NC3=CC(Cl)=CC=C3N=2)=C1 JLXAVOQTRVUYKG-UHFFFAOYSA-N 0.000 claims description 2
• PRPOBZJPAWDSGQ-UHFFFAOYSA-N 8-chloro-4-[3-(2-methylpyridin-4-yl)phenyl]-7-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(Cl)=C(C=C3N=2)C(F)(F)F)=C1 PRPOBZJPAWDSGQ-UHFFFAOYSA-N 0.000 claims description 2
• HRSCABPISYBZJE-UHFFFAOYSA-N 8-chloro-7-methyl-4-(3-pyrazin-2-ylphenyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(Cl)C(C)=CC=2N=C1C(C=1)=CC=CC=1C1=CN=CC=N1 HRSCABPISYBZJE-UHFFFAOYSA-N 0.000 claims description 2
• YJSYRZKLIDMQGG-UHFFFAOYSA-N 8-fluoro-4-[3-(2-methylpyridin-4-yl)phenyl]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(F)=CC=C3N=2)=C1 YJSYRZKLIDMQGG-UHFFFAOYSA-N 0.000 claims description 2
• QRDOMCFVXRYHRK-UHFFFAOYSA-N 8-methyl-4-(3-pyridin-4-ylphenyl)-7-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound N=1C=2C=C(C(F)(F)F)C(C)=CC=2NC(=O)CC=1C(C=1)=CC=CC=1C1=CC=NC=C1 QRDOMCFVXRYHRK-UHFFFAOYSA-N 0.000 claims description 2
• 230000006806 disease prevention Effects 0.000 claims description 2
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
• 125000005843 halogen group Chemical group 0.000 claims 12
• NBKPYZLFZCYJJE-UHFFFAOYSA-N 4-(3-pyridin-4-ylphenyl)-7-(2,2,2-trifluoroethoxy)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(OCC(F)(F)F)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=NC=C1 NBKPYZLFZCYJJE-UHFFFAOYSA-N 0.000 claims 1
• PXNOUTUNFINTTA-UHFFFAOYSA-N 4-[3-(2,6-dimethylpyridin-4-yl)phenyl]-7-(2,2,2-trifluoroethoxy)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound CC1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(=C(OCC(F)(F)F)C=C3N=2)C(F)(F)F)=C1 PXNOUTUNFINTTA-UHFFFAOYSA-N 0.000 claims 1
• CHTAULFZQPVWNJ-UHFFFAOYSA-N 4-[3-(2-ethylpyridin-4-yl)phenyl]-7-methyl-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=NC(CC)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(=C(C)C=C3N=2)C(F)(F)F)=C1 CHTAULFZQPVWNJ-UHFFFAOYSA-N 0.000 claims 1
• XUPVYWSSTOVIOJ-UHFFFAOYSA-N 4-[3-[2-(hydroxymethyl)pyridin-4-yl]phenyl]-7-methyl-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(C)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=NC(CO)=C1 XUPVYWSSTOVIOJ-UHFFFAOYSA-N 0.000 claims 1
• VMEZSFFCHLCBBK-UHFFFAOYSA-N 7,8-dichloro-4-(3-pyridin-4-ylphenyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound N=1C=2C=C(Cl)C(Cl)=CC=2NC(=O)CC=1C(C=1)=CC=CC=1C1=CC=NC=C1 VMEZSFFCHLCBBK-UHFFFAOYSA-N 0.000 claims 1
• HXTQTHUBKDBECJ-UHFFFAOYSA-N 7,8-dichloro-4-[3-(2,6-dimethylpyridin-4-yl)phenyl]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound CC1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(Cl)=C(Cl)C=C3N=2)=C1 HXTQTHUBKDBECJ-UHFFFAOYSA-N 0.000 claims 1
• CMLVJJVYIVBZNH-UHFFFAOYSA-N 7,8-dichloro-4-[3-(2-methylpyridin-4-yl)phenyl]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(Cl)=C(Cl)C=C3N=2)=C1 CMLVJJVYIVBZNH-UHFFFAOYSA-N 0.000 claims 1
• XJKJJKMFTRWVGB-UHFFFAOYSA-N 7-methoxy-4-(3-pyridin-3-ylphenyl)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(OC)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=CN=C1 XJKJJKMFTRWVGB-UHFFFAOYSA-N 0.000 claims 1
• JNFNUQBEVWFFJC-UHFFFAOYSA-N 7-methyl-4-(3-pyrazin-2-ylphenyl)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(C)=CC=2N=C1C(C=1)=CC=CC=1C1=CN=CC=N1 JNFNUQBEVWFFJC-UHFFFAOYSA-N 0.000 claims 1
• CWZIXKLALYDKHJ-UHFFFAOYSA-N 8-chloro-7-methyl-4-[3-(2-methylpyridin-4-yl)phenyl]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(Cl)=C(C)C=C3N=2)=C1 CWZIXKLALYDKHJ-UHFFFAOYSA-N 0.000 claims 1
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 315
• 239000007787 solid Substances 0.000 description 286
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 251
• 239000000203 mixture Substances 0.000 description 126
• 239000006260 foam Substances 0.000 description 115
• 235000019439 ethyl acetate Nutrition 0.000 description 103
• 239000003921 oil Substances 0.000 description 95
• 235000019198 oils Nutrition 0.000 description 95
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 94
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 90
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 88
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 75
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 74
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 74
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 69
• 239000000741 silica gel Substances 0.000 description 64
• 229910002027 silica gel Inorganic materials 0.000 description 64
• 239000000243 solution Substances 0.000 description 62
• SAHCRZHMDWJEMU-UHFFFAOYSA-N tert-butyl n-[2-amino-4-(trifluoromethyl)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(C(F)(F)F)C=C1N SAHCRZHMDWJEMU-UHFFFAOYSA-N 0.000 description 59
• 238000004440 column chromatography Methods 0.000 description 58
• 239000002904 solvent Substances 0.000 description 58
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 56
• 238000006243 chemical reaction Methods 0.000 description 55
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• 239000000126 substance Substances 0.000 description 54
• 239000012267 brine Substances 0.000 description 52
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 52
• 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 51
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
• VTSJYKYERZLMEK-UHFFFAOYSA-N tert-butyl n-[2-amino-5-(2,2,2-trifluoroethoxy)-4-(trifluoromethyl)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(OCC(F)(F)F)=C(C(F)(F)F)C=C1N VTSJYKYERZLMEK-UHFFFAOYSA-N 0.000 description 51
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 50
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