3-(Dimethylamino)pyrrolidine → HCID 69203696, compound

HRID 2114109Notes

Reaction equation

HRID 2114109 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][N:32]([CH3:38])[CH:33]1[CH2:37][CH2:36][NH:35][CH2:34]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:35]5[CH2:36][CH2:37][CH:33]([N:32]([CH3:38])[CH3:31])[CH2:34]5)[CH:3]=4)[CH:9]=3)=[CH:16][CH:17]=2)=[O:22])[CH2:27][CH2:26]1

Participants

3

Reactant 2

HCID 27585193-(Dimethylamino)pyrrolidineHCID 44578670HCID 44578670, compound

Product 1

HCID 69203696HCID 69203696, 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 3(dimethylamino)pyrrolidine (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-(3-dimethylaminopyrrolidin-1-yl)isonicotinamide (38 mg). NMR; δH [2H6]—DMSO includes 10.28,(1H, s), 8.62,(1H, t), 8.20,(1H, d), 7.93,(2H, d), 7.71,(1H, dd), 7.65,(1H, d), 7.44,(2H, d), 7.30,(1H, d), 6.98,(1H, d), 6.87,(1H, s), 3.72,(1H, m), 3.62,(1H, m), 3.37,(1H, m), 3.16,(3H, m), 2.80,(1H, b), 2.21,(9H, m), 1.81,(1H, m), 1.04,(1H, m), 0.43,(2H, m), 0.24,(2H, m). LCMS: retention time 2.55 min, MH+498.

Workup

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

Sources & evidence

ORD record
ord-d2b340e1b0b449e2aefe251fe3fb957d
Source dataset
uspto-grants-2008_10
Patent number
US07432289B2

Reaction notes

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