Ammonia → HCID 57965575, compound

HRID 69543Notes

Reaction equation

[F:1][C:2]([F:45])([F:44])[C:3]1[CH:4]=[C:5]([C:13]([CH3:43])([CH3:42])[C:14]([N:16]([CH3:41])[C:17]2[C:18]([C:33]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][C:34]=3[CH3:40])=[CH:19][C:20]([C:23]3[CH2:24][CH2:25][C@:26]([CH3:32])([C:28](OC)=[O:29])[N:27]=3)=[N:21][CH:22]=2)=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[NH3:46]>CO>[F:11][C:9]([F:12])([F:10])[C:7]1[CH:6]=[C:5]([C:13]([CH3:43])([CH3:42])[C:14]([N:16]([CH3:41])[C:17]2[C:18]([C:33]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][C:34]=3[CH3:40])=[CH:19][C:20]([C:23]3[CH2:24][CH2:25][C@:26]([CH3:32])([C:28]([NH2:46])=[O:29])[N:27]=3)=[N:21][CH:22]=2)=[O:15])[CH:4]=[C:3]([C:2]([F:44])([F:45])[F:1])[CH:8]=1

Participants

Conditions

Temperature: 20 °C

Procedure

Methyl (2R)-5-[5-[{2-[3,5-bis(trifluoromethyl)phenyl]-2-methylpropanoyl}(methyl)amino]-4-(4-fluoro-2-methylphenyl)pyridin-2-yl]-2-methyl-3,4-dihydro-2H-pyrrole-2-carboxylate (Intermediate 23 1.06 Kg) was suspended in 20.44 L of 7M ammonia in methanol. The mixture was gently stirred for at least 5 days at 20° C. The mixture was concentrated by half by distillation at atmospheric pressure. The solution obtained was then cooled to 40° C. and stirred for 1 h. The slurry obtained was then cooled to 0° C. over 3 h and aged at 0° C. for 2 h. The title compound was then isolated by filtration and the cake washed with ice cold methanol (1.1 L). The wet cake was dried at 40° C./vacuum to yield the title compound (841.3 g).

Workup

concentrationThe mixture was concentrated by half by distillation at atmospheric pressure
customThe solution obtained
temperaturewas then cooled to 40° C.
stirringstirred for 1 h
customThe slurry obtained
temperaturewas then cooled to 0° C. over 3 h

Sources & evidence

ORD record: ord-acdd0a00555d450b937ab091085383c2
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822504B2

Reaction notes

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