3,5-Dimethylpiperidine → HCID 69203170, compound

HRID 2114112Notes

Reaction equation

HRID 2114112 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[CH2:37][CH:36]([CH3:38])[CH2:35][NH:34][CH2:33]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:34]5[CH2:35][CH:36]([CH3:38])[CH2:37][CH:32]([CH3:31])[CH2:33]5)[CH:3]=4)[CH:9]=3)=[CH:16][CH:17]=2)=[O:22])[CH2:27][CH2:26]1

Participants

3

Reactant 2

HCID 1182593,5-DimethylpiperidineHCID 44578670HCID 44578670, compound

Product 1

HCID 69203170HCID 69203170, 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 3,5-dimethylpiperidine (1 ml) was heated at 120° C. for 18 h in a sealed tube. The reaction was concentrated under vacuum, the residue purified by preparative HPLC, to give, after evaporation of the solvents under vacuum N-(4′-{[(cyclopropylmethyl)amino]carbonyl}-6-methyl-1,1′-biphenyl-3-yl)-2-(3,5-dimethylpiperidin-1-yl)isonicotinamide. NMR; δH [2H6] —DMSO 10.29,(1H, s), 8.62,(1H, t), 8.21,(1H, d), 7.93,(2H, d), 7.70,(1H, dd), 7.65,(1H, d), 7.44,(2H, d), 7.30,(1H, d), 7.20,(1H, s), 6.98,(1H, d), 4.35,(2H, m), 3.16,(2H, t), 2.30,(2H, t), 2.20,(3H, s), 1.78,(1H, m), 1.57,(2H, m), 1.04,(1H, m), 0.91,(6H, d), 0.80,(1 H, q), 0.43,(2H, m), 0.24,(2H, m). LCMS: retention time 3.61 min, MH+497.

Workup

  1. concentrationThe reaction was concentrated under vacuum
  2. customthe residue purified by preparative HPLC
  3. customto give
  4. customafter evaporation of the solvents under vacuum N-(4′-{[(cyclopropylmethyl)amino]carbonyl}-6-methyl-1,1′-biphenyl-3-yl)-2-(3,5-dimethylpiperidin-1-yl)isonicotinamide

Sources & evidence

ORD record
ord-25f1df12ff21436ca73cec981517d8ab
Source dataset
uspto-grants-2008_10
Patent number
US07432289B2

Reaction notes

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