Cyclobutylamine → HCID 44578748, compound

HRID 2114114Notes

Reaction equation

HRID 2114114 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].[CH:31]1([NH2:35])[CH2:34][CH2:33][CH2:32]1>CS(C)=O>[CH:31]1([NH:35][C:2]2[CH:3]=[C:4]([CH:28]=[CH:29][N:30]=2)[C:5]([NH:7][C:8]2[CH:9]=[C:10]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([NH:23][CH2:24][CH:25]4[CH2:27][CH2:26]4)=[O:22])=[CH:17][CH:16]=3)[C:11]([CH3:14])=[CH:12][CH:13]=2)=[O:6])[CH2:34][CH2:33][CH2:32]1

Participants

4

Reactant 2

HCID 75645CyclobutylamineHCID 44578670HCID 44578670, compound

Product 1

HCID 44578748HCID 44578748, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 2-chloro-N-(4′-{[(cyclopropylmethyl)amino]carbonyl}-6-methyl-1,1′-biphenyl-3-yl)isonicotinamide (50 mg, 0.12 mmol) and cyclobutylamine (1 ml) in DMSO (1 ml) was heated at 140° C. for 72 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 2-(cyclobutylamino)-N-(4′-{[(Cyclopropylmethyl)amino]carbonyl}-6-methyl-1,1′-biphenyl-3-yl)isonicotinamide. NMR; δH [2H6]—DMSO 10.27,(1H, s), 8.62,(1H, t), 8.08,(1H, d), 7.93,(2H, d), 7.70-7.65,(2H, m), 7.43,(2H, d), 7.28,(1H, d), 7.06,(1H, d), 6.90,(1H, d), 6.81,(1H, s), 4.30,(1H, m), 3.16,(2H, t), 2.26,(2H, m), 2.20,(3H, s), 1.87,(2H, m), 1.67,(2H, m), 1.04,(1H, m), 0.43,(2H, m), 0.24,(2H, m). LCMS: retention time 2.82 min, MH+455.

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 2-(cyclobutylamino)-N-(4′-{[(Cyclopropylmethyl)amino]carbonyl}-6-methyl-1,1′-biphenyl-3-yl)isonicotinamide

Sources & evidence

ORD record
ord-ff0ed6d59f35428998d629e3a6fcb6d3
Source dataset
uspto-grants-2008_10
Patent number
US07432289B2

Reaction notes

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