3-Methylpiperidine → HCID 69200860, compound

HRID 2114111Notes

Reaction equation

HRID 2114111 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][CH2:36][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][CH2:36][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 790813-MethylpiperidineHCID 44578670HCID 44578670, compound

Product 1

HCID 69200860HCID 69200860, 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-methylpiperidine (1 ml) was heated at 120° C. for 18 h in a sealed tube. The reaction was concentrated under vacuum, the residue chromatographed on an SPE (C18) eluting with a water/acetonitrile gradient, to give, after evaporation of the solvents under vacuum N-(4′-{[(cyclopropylmethyl)amino]carbonyl}-6-methyl-1,1′-biphenyl-3-yl)-2-(3-methylpiperidin-1-yl)isonicotinamide (16 mg). NMR; δH [2H6]—DMSO includes 10.28,(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), 4.26,(2H, m), 3.16,(2H, t), 2.80,(1H, m), 2.20,(3H, s), 1.78,(1H, m), 1.68,(1H, m), 1.57,(1H, m), 1.45,(1H, m), 1.15,(1H, m), 1.04,(1H, m),0.91,(2H, d), 0.43,(2H, m), 0.24,(2H, m). LCMS: retention time 3.54 min, MH+483.

Workup

  1. concentrationThe reaction was concentrated under vacuum
  2. customthe residue chromatographed on an SPE (C18)
  3. washeluting with a water/acetonitrile gradient
  4. customto give
  5. customafter evaporation of the solvents under vacuum N-(4′-{[(cyclopropylmethyl)amino]carbonyl}-6-methyl-1,1′-biphenyl-3-yl)-2-(3-methylpiperidin-1-yl)isonicotinamide (16 mg)

Sources & evidence

ORD record
ord-b8cf29d872ed493ba7ff2beb3d3a4fe8
Source dataset
uspto-grants-2008_10
Patent number
US07432289B2

Reaction notes

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