HCID 67095303, compound → HCID 75631953, compound

HRID 909099Notes

Reaction equation

HRID 909099 reaction equation
[Cl:1][C:2]1[C:3]([F:28])=[C:4]([CH:8]2[C:12]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[F:22])([C:13]#[N:14])[CH:11]([CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:10][NH:9]2)[CH:5]=[CH:6][CH:7]=1.[CH3:29][N:30]1[CH:35]=[CH:34][C:33]([NH:36][C:37](N2C=CN=C2)=[O:38])=[CH:32][C:31]1=[O:44]>C(Cl)Cl>[CH3:29][N:30]1[CH:35]=[CH:34][C:33]([NH:36][C:37]([N:9]2[CH2:10][CH:11]([CH2:23][C:24]([CH3:25])([CH3:27])[CH3:26])[C:12]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[F:22])([C:13]#[N:14])[CH:8]2[C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=2[F:28])=[O:38])=[CH:32][C:31]1=[O:44]

Participants

4

Reactant 2

HCID 67095303HCID 67095303, compoundHCID 67095372rac-(2S,3S,4S)-2-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-4-(2,2-dimethyl-propyl)-pyrrolidine-3-carbonitrile

Product 1

HCID 75631953HCID 75631953, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of rac-(2S,3S,4S)-2-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-4-(2,2-dimethyl-propyl)-pyrrolidine-3-carbonitrile (15.8 mg, 0.0373 mmol) and imidazole-1-carboxylic acid (1-methyl-2-oxo-1,2-dihydro-pyridin-4-yl)-amide (76.3 mg, 0.105 mmol) in CH2Cl2 (1.5 mL) was stirred at rt for 1 day. The reaction mixture was then purified by flash column to rac (2S,3S,4S)-2-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-3-cyano-4-(2,2-dimethyl-propyl)-pyrrolidine-1-carboxylic acid (1-methyl-2-oxo-1,2-dihydro-pyridin-4-yl)-amide (19.7 mg, 92.1%). HRMS (ES+) m/z Calcd for C29H28Cl2F2N4O2+H [(M+H)+]: 573.1630; Found: 573.1629.

Workup

  1. customThe reaction mixture was then purified by flash column to rac (2S,3S,4S)-2-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-3-cyano-4-(2,2-dimethyl-propyl)-pyrrolidine-1-carboxylic acid (1-methyl-2-oxo-1,2-dihydro-pyridin-4-yl)-amide (19.7 mg, 92.1%)

Sources & evidence

ORD record
ord-6ea88c6adc624236997f24c3c3f34271
Source dataset
uspto-grants-2011_09
Patent number
US08017607B2

Reaction notes

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