Dimethylformamide → 1-(2-Methoxy-5-trifluoromethyl-phenyl)-3-{3-[8-(2-pyridin-4-yl-imidazol-1-yl)-imidazo[1,2-a]pyrazin-6-yl]-phenyl}-urea

HRID 457673Notes

Reaction equation

HRID 457673 reaction equation
Br[C:2]1([C:22]2[CH:23]=[C:24]([NH2:28])[CH:25]=[CH:26][CH:27]=2)[CH2:7][N:6]2[CH:8]=[CH:9][N:10]=[C:5]2[C:4]([N:11]2[CH:15]=[CH:14][N:13]=[C:12]2[C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)=[N:3]1.[N:29]([C:32]1[CH:37]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:35]=[CH:34][C:33]=1[O:42][CH3:43])=[C:30]=[O:31].CN(C=O)C>ClCCl>[CH3:43][O:42][C:33]1[CH:34]=[CH:35][C:36]([C:38]([F:41])([F:40])[F:39])=[CH:37][C:32]=1[NH:29][C:30]([NH:28][C:24]1[CH:25]=[CH:26][CH:27]=[C:22]([C:2]2[N:3]=[C:4]([N:11]3[CH:15]=[CH:14][N:13]=[C:12]3[C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[C:5]3[N:6]([CH:8]=[CH:9][N:10]=3)[CH:7]=2)[CH:23]=1)=[O:31]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 11983909Benzene, 2-isocyanato-1-methoxy-4-(trifluoromethyl)-HCID 184403173-[6-Bromo-8-(2-pyridin-4-yl-imidazol-1-yl)-imidazo[1,2-a]pyrazin-6-yl]-phenylamine

Product 1

HCID 99379601-(2-Methoxy-5-trifluoromethyl-phenyl)-3-{3-[8-(2-pyridin-4-yl-imidazol-1-yl)-imidazo[1,2-a]pyrazin-6-yl]-phenyl}-ureaYield 89.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-[6-Bromo-8-(2-pyridin-4-yl-imidazol-1-yl)-imidazo[1,2-a]pyrazin-6-yl]-phenylamine (5) (400 mg), 2-isocyanato-1-methoxy-4-trifluoromethyl-benzene (246 mg), in dichloromethane (DCM) (3 ml) and DMF (0.5 ml) is stirred at room temperature for 16 hr. The mixture is concentrated in vacuo, the residue slurried with diethyl ether/methanol (20:1), and filtered to give 1-(2-Methoxy-5-trifluoromethyl-phenyl)-3-{3-[8-(2-pyridin-4-yl-imidazol-1-yl)-imidazo[1,2-a]pyrazin-6-yl]-phenyl}-urea (6) (468 mg) as a white solid.

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. filtrationfiltered

Sources & evidence

ORD record
ord-942889ebb28e4855bd9282188727f8e7
Source dataset
uspto-grants-2007_03
Patent number
US07189723B2

Reaction notes

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