1,1'-Carbonyldiimidazole → N-benzyl-2-(3-(2,2-dimethoxyethyl)-3-(4-fluorophenyl)ureido)-4-methylthiazole-5-carboxamide

HRID 2067309Notes

Reaction equation

HRID 2067309 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])=[C:5]([CH3:7])[N:6]=1.[C:18](N1C=CN=C1)(N1C=CN=C1)=[O:19].[CH3:30][O:31][CH:32]([O:42][CH3:43])[CH2:33][NH:34][C:35]1[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=1>O1CCCC1>[CH2:11]([NH:10][C:8]([C:4]1[S:3][C:2]([NH:1][C:18]([N:34]([CH2:33][CH:32]([O:31][CH3:30])[O:42][CH3:43])[C:35]2[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=2)=[O:19])=[N:6][C:5]=1[CH3:7])=[O:9])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 210824N-Benzyl-2-imino-4-methyl-2,3-dihydro-1,3-thiazole-5-carboximidic acidHCID 63686639N-(2,2-dimethoxyethyl)-4-fluoroaniline

Product 1

HCID 86645283N-benzyl-2-(3-(2,2-dimethoxyethyl)-3-(4-fluorophenyl)ureido)-4-methylthiazole-5-carboxamideYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-N-benzyl-4-methylthiazole-5-carboxamide (0.37 g, 1.50 mmol) in tetrahydrofuran (20 mL) was added 1,1′-carbonyldiimidazole (0.31 g, 1.91 mmol) at ambient temperature. The resulting reaction mixture was stirred at ambient temperature for 11 hours, followed by the addition of N-(2,2-dimethoxyethyl)-4-fluoroaniline (0.40 g, 2.00 mmol). The reaction mixture was kept stirring for 17 hour at ambient temperature. The solvent was removed in vacuo, and the residue was purified by column chromatography to afford the title compound in 68% yield (0.48 g): 1H NMR (300 MHz, CDCl3) δ 7.36-7.12 (m, 10H), 5.89 (t, J=5.7 Hz, 1H), 4.61 (t, J=5.4 Hz, 1H), 4.53 (d, J=5.4 Hz, 2H), 3.76 (t, J=5.7 Hz, 2H), 3.31 (s, 6H), 2.51 (s, 3H); MS (ES+) m/z 473.4 (M+1).

Workup

  1. customThe resulting reaction mixture
  2. stirringThe reaction mixture was kept stirring for 17 hour at ambient temperature
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-2dca88e9e9644973bfbed02fb16e88f9
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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