2-Methylpyrrolidine → HCID 69202406, compound

HRID 2114108Notes

Reaction equation

HRID 2114108 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][N:30]=1)[C:5]([NH:7][C:8]1[CH:9]=[C:10]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([NH:23][CH2:24][CH:25]3[CH2:27][CH2:26]3)=[O:22])=[CH:17][CH:16]=2)[C:11]([CH3:14])=[CH:12][CH:13]=1)=[O:6].[CH3:31][CH:32]1[CH2:36][CH2:35][CH2:34][NH:33]1>>[CH:25]1([CH2:24][NH:23][C:21]([C:18]2[CH:19]=[CH:20][C:15]([C:10]3[C:11]([CH3:14])=[CH:12][CH:13]=[C:8]([NH:7][C:5](=[O:6])[C:4]4[CH:28]=[CH:29][N:30]=[C:2]([N:33]5[CH2:34][CH2:35][CH2:36][CH:32]5[CH3:31])[CH:3]=4)[CH:9]=3)=[CH:16][CH:17]=2)=[O:22])[CH2:27][CH2:26]1

Participants

3

Reactant 2

HCID 130032-MethylpyrrolidineHCID 44578670HCID 44578670, compound

Product 1

HCID 69202406HCID 69202406, compound

Procedure

A solution of 2-chloro-N-(4′-{[(cyclopropylmethyl)amino]carbonyl}-6-methyl-1,1′-biphenyl-3-yl)isonicotinamide (50 mg, 0.12 mmol) in 2-methylpyrrolidine (1 ml) was heated at 120° C. for 18 h in a sealed tube. The reaction was concentrated under vacuum, the residue triturated with water to give N-(4′-{[(cyclopropylmethyl)amino]carbonyl}-6-methyl-1,1′-biphenyl-3-yl)-2-(2-methylpyrrolidin-1-yl)isonicotinamide (35 mg). NMR; δH [2H6]—DMSO 10.27,(1H, s), 8.62,(1H, t), 8.20,(1H, d), 7.93,(2H, d), 7.70,(1H, d), 7.66,(1H, s), 7.44,(2H, d), 7.30,(1H, d), LCMS: retention time 2.89 min, MH+469.

Workup

  1. concentrationThe reaction was concentrated under vacuum
  2. customthe residue triturated with water

Sources & evidence

ORD record
ord-8562df637f20470ab3af75c4cba755e7
Source dataset
uspto-grants-2008_10
Patent number
US07432289B2

Reaction notes

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