Dimethylamine → HCID 44578671, compound

HRID 2114100Notes

Reaction equation

HRID 2114100 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][NH:32][CH3:33]>CN(C=O)C>[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:32]([CH3:33])[CH3:31])[CH:3]=4)[CH:9]=3)=[CH:16][CH:17]=2)=[O:22])[CH2:27][CH2:26]1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 44578670HCID 44578670, compound

Product 1

HCID 44578671HCID 44578671, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Chloro-N-(4′-{[(cyclopropylmethyl)amino]carbonyl}-6-methyl-1,1′-biphenyl-3-yl)isonicotinamide and dimethylamine (40% in water) in DMF (1 ml) were heated at 85° C. for 96 h in a sealed tube. The reaction mixture was concentrated under vacuum, purified by preparative HPLC and the product fractions reduced to dryness under vacuum to give N-(4′-{[(cyclopropylmethyl)amino]carbonyl}-6-methyl-1,1′-biphenyl-3-yl)-2-(dimethylamino)isonicotinamide. NMR; δH [2H6]—DMSO 10.29,(1H, s), 8.62,(1H, t), 8.22,(1H, d), 7.93,(2H, d), 7.70,(1H, dd), 7.65,(1H, d), 7.44,(2H, d), 7.30,(1H, d), 7.03,(1H, s), 6.99,(1H, d), 3.16,(2H, t), 3.07,(6H, s), 2.20,(3H, s), 1.04,(1H, m), 0.43,(2H, m), 0.24,(2H, m). LCMS: retention time 2.88 min, MH+429.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-74adee3338e1401e889dadec85c1a646
Source dataset
uspto-grants-2008_10
Patent number
US07432289B2

Reaction notes

Loading…