HCID 44578670, compound → HCID 44578746, compound

HRID 2114101Notes

Reaction equation

HRID 2114101 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(CN)CC1>[CH:25]1([CH2:24][NH:23][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])[CH2:27][CH2:26]1

Participants

3

Reactant 1

HCID 44578670HCID 44578670, compound

Product 1

HCID 44578746HCID 44578746, compoundYield 62.7%

Reagents, catalysts & solvents 1

HCID 75646CyclopropanemethanamineSolvent

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 cyclopropylmethylamine (1 ml) was heated at 85° C. for 48 h and then at 110° 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-(cyclopropylmethylamino)-N-(4′-{[(cyclopropylmethyl)amino]carbonyl}-6-methyl-1,1′-biphenyl-3-yl)isonicotinamide (17.1 mg, 32%). NMR; εH [2H6]—DMSO 10.27,(1H, s), 8.62,(1H, t), 8.08,(1H, d), 7.93,(2H, d), 7.70-7.66,(2H, m), 7.44,(2H, d), 7.28,(1H, d), 6.89-6.87,(3H, m), 3.16,(4H, m), 2.20,(3H, s), 1.04,(2H, m), 0.43,(4H, m), 0.25-0.19,(4H, m). LCMS: retention time 2.96 min, MH+455.

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-33acc3da2ad441c19b0700bc6fb0e8dc
Source dataset
uspto-grants-2008_10
Patent number
US07432289B2

Reaction notes

Loading…