HCID 44578670, compound → HCID 86595278, compound

HRID 2114104Notes

Reaction equation

HRID 2114104 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]>C1(N)CCCCC1>[CH:25]1([CH2:24][NH:23][C:21]([C:18]2[CH:17]=[CH:16][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]=[CH:2][CH:3]=4)[CH:9]=3)=[CH:20][CH:19]=2)=[O:22])[CH2:27][CH2:26]1

Participants

3

Reactant 1

HCID 44578670HCID 44578670, compound

Product 1

HCID 86595278HCID 86595278, compoundYield 31.1%

Reagents, catalysts & solvents 1

HCID 7965CyclohexylamineSolvent

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 cyclohexylamine (1 ml) was heated at 110° C. for 36 h and then at 160° C. for 48 h in a sealed tube. The reaction was concentrated under vacuum, the residue triturated with water and purified by preparative HPLC. The solvent was evaporated under vacuum to give 2-cyclohexylamino)-N-(4′-{[(cyclopropylmethyl)amino]carbonyl}-6-methyl-1,1′-biphenyl-3-yl)isonicotinamide (14.4 mg). NMR; δH [2H6]—DMSO 10.26,(1H, s), 8.62,(1H, t), 8.07,(1H, d), 7.92,(2H, d), 7.69-7.66,(2H, m), 7.43,(2H, d), 7.28,(1H, d), 6.84,(2H, m), 6.67,(1H, d), 3.72,(1H, m), 3.16,(2H, t), 2.19,(3H, s), 1.90,(2H, m), 1.70,(2H, m), 1.57,(1H, m), 1.31,(2H, m), 1.18,(3H, m), 1.04,(1H, m), 0.24,(2h, m). LCMS: retention time 3.14 min, MH+483.

Workup

  1. concentrationThe reaction was concentrated under vacuum
  2. customthe residue triturated with water
  3. custompurified by preparative HPLC
  4. customThe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-81bd99b089ca4cd0831c4cdcf7520c6d
Source dataset
uspto-grants-2008_10
Patent number
US07432289B2

Reaction notes

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