Dimethylformamide → 1-o-Tolyl-3-{3-[8-(4-p-tolyl-imidazol-1-yl)-imidazo[1,2-a]pyrazin-6-yl]-phenyl}-urea

HRID 1372929Notes

Reaction equation

HRID 1372929 reaction equation
[C:1]1([CH3:28])[CH:6]=[CH:5][C:4]([C:7]2[N:8]=[CH:9][N:10]([C:12]3[C:13]4[N:14]([CH:25]=[CH:26][N:27]=4)[CH:15]=[C:16]([C:18]4[CH:19]=[C:20]([NH2:24])[CH:21]=[CH:22][CH:23]=4)[N:17]=3)[CH:11]=2)=[CH:3][CH:2]=1.[N:29]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[CH3:38])=[C:30]=[O:31].CN(C=O)C>ClCCl>[C:33]1([CH3:38])[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=1[NH:29][C:30]([NH:24][C:20]1[CH:21]=[CH:22][CH:23]=[C:18]([C:16]2[N:17]=[C:12]([N:10]3[CH:11]=[C:7]([C:4]4[CH:3]=[CH:2][C:1]([CH3:28])=[CH:6][CH:5]=4)[N:8]=[CH:9]3)[C:13]3[N:14]([CH:25]=[CH:26][N:27]=3)[CH:15]=2)[CH:19]=1)=[O:31]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 691942-Tolyl isocyanateHCID 210728853-[8-(4-p-Tolyl-imidazol-1-yl)-imidazo[1,2-a]pyrazin-6-yl]-phenylamine

Product 1

HCID 103912511-o-Tolyl-3-{3-[8-(4-p-tolyl-imidazol-1-yl)-imidazo[1,2-a]pyrazin-6-yl]-phenyl}-ureaYield 59.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-[8-(4-p-tolyl-imidazol-1-yl)-imidazo[1,2-a]pyrazin-6-yl]-phenylamine (5) (50 mg), 1-isocyanato-2-methyl-benzene (18 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-o-tolyl-3-{3-[8-(4-p-tolyl-imidazol-1-yl)-imidazo[1,2-a]pyrazin-6-yl]-phenyl}-urea (6) (40 mg) as a cream solid.

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. filtrationfiltered

Sources & evidence

ORD record
ord-a4121b4de3514b80b68a513f094efe5b
Source dataset
uspto-grants-2007_01
Patent number
US07160885B2

Reaction notes

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