HCID 44578670, compound → Isonicotinamide

HRID 2114105Notes

Reaction equation

HRID 2114105 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][N:30]=1)[C:5]([NH:7]C1C=C(C2C=CC(C(NCC3CC3)=O)=CC=2)C(C)=CC=1)=[O:6]>C1(N)CC1>[C:5]([NH2:7])(=[O:6])[C:4]1[CH:28]=[CH:29][N:30]=[CH:2][CH:3]=1

Participants

3

Reactant 1

HCID 44578670HCID 44578670, compound

Product 1

HCID 15074IsonicotinamideYield 40.9%

Reagents, catalysts & solvents 1

HCID 69828CyclopropylamineSolvent

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 cyclopropylamine (2 ml) was heated at 85° C. for 48 h and then at 110° C. for 72 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-(cyclopropylamino)-N-4′-{[(cyclopropylmethyl)amino]carbonyl}-6-methyl-1,1′-biphenyl-3-yl)isonicotinamide (6 mg). NMR; δH [2H6]—DMSO 10.32,(1H, s), 8.62,(1H, t), 8.14,(1H, d), 7.93,(2H, d), 7.71-7.67,(2H, m), 7.44,(2H, d), 7.29,(1H, d), 7.05,(1H, d), 7.00-6.98,(2H, m), 3.16,(2H, t), 2.55,(1H, m), 2.20,(3H, s), 1.05,(1H, m), 0.71,(2H, m), 0.43,(4H, m), 0.24,(2H, m). LCMS: retention time 2.74 min, MH+441.

Workup

  1. customat 110° C. for 72 h in a sealed tube.The reaction
  2. concentrationwas concentrated under vacuum
  3. customthe residue triturated with water
  4. custompurified by preparative HPLC
  5. customThe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-08aa51e541de48ba8e4b73454257ce0c
Source dataset
uspto-grants-2008_10
Patent number
US07432289B2

Reaction notes

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