HCID 44578670, compound → HCID 44578710, compound

HRID 2114107Notes

Reaction equation

HRID 2114107 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]>CC1CCNCC1>[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:30]5[CH2:29][CH2:28][CH:4]([CH3:5])[CH2:3][CH2:2]5)[CH:3]=4)[CH:9]=3)=[CH:16][CH:17]=2)=[O:22])[CH2:27][CH2:26]1

Participants

3

Reactant 1

HCID 44578670HCID 44578670, compound

Product 1

HCID 44578710HCID 44578710, compoundYield 134.7%

Reagents, catalysts & solvents 1

HCID 693814-MethylpiperidineSolvent

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 4-methylpiperidine (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-(4-methylpiperidin-1-yl)isonicotinamide (39 mg). NMR; δH [2H6]—DMSO 10.28,(1H, s), 8.62,(1H, t), 8.22,(11, d), 7.93,(2H, d), 7.71,(1H, d), 7.64,(1H, s), 7.44,(2H, d), 7.30,(1H, d), 7.21,(1H, s), 7.00,(1H, d), 4.35,(2H, m), 3.16,(2H, t), 2.83,(2H, m), 2.20,(3H, s), 1.69-1.60,(3H, m), 1.07,(3H, m), 0.92,(3H, d), 0.43,(2H, m), 0.24,(2H, m). LCMS: retention time 3.55 min, MH+483.

Workup

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

Sources & evidence

ORD record
ord-34c40ead81294af99f44572bd0346972
Source dataset
uspto-grants-2008_10
Patent number
US07432289B2

Reaction notes

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