(1-Methylpyrazol-3-yl)methanamine → rac-(2'S,3'S,4'S)-6-chloro-2'-(3-chloro-2-fluoro-phenyl)-4'-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-1'-carboxylic acid (1-methyl-1H-pyrazol-3-ylmethyl)-amide

HRID 2065427Notes

Reaction equation

HRID 2065427 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:31])[C:10]3([CH:14]([CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:13][N:12]([C:20](Cl)=[O:21])[CH:11]3[C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:24]=3[F:30])[C:5]2=[CH:4][CH:3]=1.[CH3:32][N:33]1[CH:37]=[CH:36][C:35]([CH2:38][NH2:39])=[N:34]1>C(N(CC)CC)C>[CH3:32][N:33]1[CH:37]=[CH:36][C:35]([CH2:38][NH:39][C:20]([N:12]2[CH2:13][CH:14]([CH2:15][C:16]([CH3:19])([CH3:17])[CH3:18])[C:10]3([C:5]4[C:6](=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=4)[NH:8][C:9]3=[O:31])[CH:11]2[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:24]=2[F:30])=[O:21])=[N:34]1

Participants

4

Reactant 2

HCID 7019419(1-Methylpyrazol-3-yl)methanamineHCID 76776161rac-(2'S,3'S,4'S)-6-chloro-2'-(3-chloro-2-fluoro-phenyl)-4'-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-1'-carbonyl chloride

Product 1

HCID 76021613rac-(2'S,3'S,4'S)-6-chloro-2'-(3-chloro-2-fluoro-phenyl)-4'-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-1'-carboxylic acid (1-methyl-1H-pyrazol-3-ylmethyl)-amide

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In a manner similar to the method described in Example 9, rac-(2′S,3′S,4′S)-6-chloro-2′-(3-chloro-2-fluoro-phenyl)-4′-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3′-pyrrolidine]-1′-carbonyl chloride prepared in Example 8 (57 mg, 0.12 mmol) was reacted with (1-methyl-1H-pyrazol-3-yl)methylamine (Oakwood) (20 mg, 0.18 mmol) and triethylamine to give rac-(2′S,3′S,4′S)-6-chloro-2′-(3-chloro-2-fluoro-phenyl)-4′-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3′-pyrrolidine]-1′-carboxylic acid (1-methyl-1H-pyrazol-3-ylmethyl)-amide as a white solid (Yield, 18 mg, 27%).

Workup

  1. customto give

Sources & evidence

ORD record
ord-d629864378c04535ad276479f5f3e281
Source dataset
uspto-grants-2012_10
Patent number
US08288431B2

Reaction notes

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