HCID 44578670, compound → Isonicotinamide

HRID 2114106Notes

Reaction equation

HRID 2114106 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]>C(NCC)C>[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 15074Isonicotinamide

Reagents, catalysts & solvents 1

HCID 8021DiethylamineSolvent

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 diethylamine (2 ml) was heated at 80° C. for 48 h and then at 110° C. for 84 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 N-(4′-{[(cyclopropylmethyl)amino]carbonyl}-6-methyl-1,1′-biphenyl-3-yl)-2-diethylamino)isonicotinamide. NMR; δH [2H6]—DMSO 10.27,(1H, s), 8.62,(1H, t), 8.19,(1H, d), 7.93,(2H, d), 7.69,(1H, dd), 7.65,(1H, d), 7.44,(2H, d), 7.30,(1H, d), 0.43,(4H, m), 0.24,(2H, m). LCMS: retention time 3.09 min, MH+457.

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-33732e4d28724b9bb3f4c28a1142879b
Source dataset
uspto-grants-2008_10
Patent number
US07432289B2

Reaction notes

Loading…