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

HRID 560545Notes

Reaction equation

HRID 560545 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].[F:30][C:31]1[CH:44]=[CH:43][C:34]([CH2:35][NH:36][CH2:37][CH:38]([O:41][CH3:42])[O:39][CH3:40])=[CH:33][CH:32]=1>O1CCCC1>[CH2:11]([NH:10][C:8]([C:4]1[S:3][C:2]([NH:1][C:18]([N:36]([CH2:37][CH:38]([O:39][CH3:40])[O:41][CH3:42])[CH2:35][C:34]2[CH:33]=[CH:32][C:31]([F:30])=[CH:44][CH:43]=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 11615438N-(2,2-dimethoxyethyl)-N-(4-fluorobenzyl)amine

Product 1

HCID 86645286N-benzyl-2-(3-(2,2-dimethoxyethyl)-3-(4-fluorobenzyl)ureido)-4-methylthiazole-5-carboxamideYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-N-benzyl-4-methylthiazole-5-carboxamide (0.31 g, 1.25 mmol) in tetrahydrofuran (20 mL) was added 1,1′-carbonyldiimidazole (0.24 g, 1.50 mmol) at ambient temperature. The resulting reaction mixture was stirred at ambient temperature for 6 hours, and N-(4-fluorobenzyl)-2,2-dimethoxyethanamine (0.35 g, 1.65 mmol) was added. The reaction mixture was stirred at ambient temperature for 17 hour. The solvent was removed in vacuo, and the residue was purified by column chromatography to afford the title compound in 77% yield (0.47 g): MS (ES+) m/z 487.4 (M+1).

Workup

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

Sources & evidence

ORD record
ord-9917ef5999cc467ea285df60485063d1
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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