Nitrogen → HCID 44547598, compound

HRID 2400322Notes

Reaction equation

HRID 2400322 reaction equation
N#N.[CH3:3][N:4]1[C:8]([C:9]#[C:10][C:11]2[CH:16]=[CH:15][N:14]3[C:17]([C:20]4[CH:21]=[C:22]([NH:26][C:27]([NH:29][CH2:30][C:31]([F:34])([F:33])[F:32])=[O:28])[CH:23]=[CH:24][CH:25]=4)=[CH:18][N:19]=[C:13]3[CH:12]=2)=[CH:7][N:6]=[CH:5]1>CO.[Pd]>[CH3:3][N:4]1[C:8]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][N:14]3[C:17]([C:20]4[CH:21]=[C:22]([NH:26][C:27]([NH:29][CH2:30][C:31]([F:32])([F:34])[F:33])=[O:28])[CH:23]=[CH:24][CH:25]=4)=[CH:18][N:19]=[C:13]3[CH:12]=2)=[CH:7][N:6]=[CH:5]1

Participants

5

Reactant 2

HCID 947NitrogenHCID 68161655HCID 68161655, compound

Product 1

HCID 44547598HCID 44547598, compoundYield 9.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To an evacuated flask back-filled with N2 containing 1-{3-[7-(3-methyl-3H-imidazol-4-ylethynyl)-imidazo[1,2-a]pyridin-3-yl]-phenyl}-3-(2,2,2-trifluoro-ethyl)-urea (65.7 mg, 0.15 mmol) in MeOH was added Pd (10 wt % on activated carbon) (25.5 mg). The flask was filled with H2 and the reaction stirred for a total of 7.5 hours. The reaction was filtered and the filtrate concentrated in vacuo. The crude product was purified by preparative HPLC to give pure product (6.1 mg). MS: [M+H]+443.

Workup

  1. additionThe flask was filled with H2
  2. filtrationThe reaction was filtered
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-f4cf5f0aa3c94afaa63dcefd9380ffc4
Source dataset
uspto-grants-2014_08
Patent number
US08796244B2

Reaction notes

Loading…