3-Isocyanatopyridine → HCID 67095422, compound

HRID 909070Notes

Reaction equation

HRID 909070 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.[N:29]([C:32]1[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=1)=[C:30]=[O:31]>C(Cl)Cl>[N:34]1[CH:35]=[CH:36][CH:37]=[C:32]([NH:29][C:30]([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:31])[CH:33]=1

Participants

4

Reactant 2

HCID 27604933-IsocyanatopyridineHCID 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 67095422HCID 67095422, compoundYield 30%

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 (40 mg, 0.095 mmol) and 3-isocyanatopyridine (Oakwood, 29.1 mg, 0.242 mmol) in CH2Cl2 (5 mL) was stirred at rt for 17 hrs. The reaction mixture was then purified by flash column to give 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 pyridin-3-ylamide (15.5 mg, 30%).

Workup

  1. customThe reaction mixture was then purified by flash column

Sources & evidence

ORD record
ord-88923da7463d4f0aacc3d9dc2ae87920
Source dataset
uspto-grants-2011_09
Patent number
US08017607B2

Reaction notes

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