JP2017514845A5 - - Google Patents

Info

Publication number

JP2017514845A5

JP2017514845A5 JP2016565665A JP2016565665A JP2017514845A5 JP 2017514845 A5 JP2017514845 A5 JP 2017514845A5 JP 2016565665 A JP2016565665 A JP 2016565665A JP 2016565665 A JP2016565665 A JP 2016565665A JP 2017514845 A5 JP2017514845 A5 JP 2017514845A5

Authority

JP

Japan

Prior art keywords

formula

compound

molar equivalents

present

amine base

Prior art date

2015-04-28

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Pending

Links

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• 150000001875 compounds Chemical class 0.000 claims 71
• 238000000034 method Methods 0.000 claims 64
• 150000001412 amines Chemical class 0.000 claims 18
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical group CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 16
• 239000003960 organic solvent Substances 0.000 claims 14
• 150000003839 salts Chemical class 0.000 claims 12
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 6
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 6
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 6
• 229910052794 bromium Inorganic materials 0.000 claims 6
• YAJYJWXEWKRTPO-UHFFFAOYSA-N 2,3,3,4,4,5-hexamethylhexane-2-thiol Chemical compound CC(C)C(C)(C)C(C)(C)C(C)(C)S YAJYJWXEWKRTPO-UHFFFAOYSA-N 0.000 claims 5
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 5
• MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims 5
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
• 239000012649 demethylating agent Substances 0.000 claims 4
• 238000004519 manufacturing process Methods 0.000 claims 4
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims 3
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims 3
• 150000004703 alkoxides Chemical class 0.000 claims 2
• QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
• 229940043279 diisopropylamine Drugs 0.000 claims 1
• 0 CO[C@](CC1)(*[C@@](*)C[C@@]1(*1)[C@@](C2)C(CC3CC3)CC[C@@]11c3c2cc2)[C@@]1Oc3c2OC Chemical compound CO[C@](CC1)(*[C@@](*)C[C@@]1(*1)[C@@](C2)C(CC3CC3)CC[C@@]11c3c2cc2)[C@@]1Oc3c2OC 0.000 description 5