1,1'-Carbonyldiimidazole → 2-(3-(2,2-dimethoxyethyl)-3-(4-fluorophenethyl)ureido)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide

HRID 560553Notes

Reaction equation

HRID 560553 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:8]([NH:10][CH2:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=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:45]=[CH:44][C:34]([CH2:35][CH2:36][NH:37][CH2:38][CH:39]([O:42][CH3:43])[O:40][CH3:41])=[CH:33][CH:32]=1>O1CCCC1>[CH3:43][O:42][CH:39]([O:40][CH3:41])[CH2:38][N:37]([CH2:36][CH2:35][C:34]1[CH:33]=[CH:32][C:31]([F:30])=[CH:45][CH:44]=1)[C:18](=[O:19])[NH:1][C:2]1[S:3][C:4]([C:8]([NH:10][CH2:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[O:9])=[C:5]([CH3:7])[N:6]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 627938962-amino-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamideHCID 63686615N-(4-fluorophenethyl)-2,2-dimethoxyethanamine

Product 1

HCID 866452872-(3-(2,2-dimethoxyethyl)-3-(4-fluorophenethyl)ureido)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamideYield 19%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide (0.50 g, 2.01 mmol) in tetrahydrofuran (30 mL) was added 1,1′-carbonyldiimidazole (0.39 g, 2.41 mmol) at ambient temperature. The resulting reaction mixture was stirred at ambient temperature for 6 hours and N-(4-fluorophenethyl)-2,2-dimethoxyethanamine (0.59 g, 2.61 mmol) was added. The reaction mixture was stired for 17 hour at ambient temperature. The solvent was removed in vacuo, and the residue was purified by column chromatography eluted with dichloromethane/methanol (4/1) to afford 2-(3-(2,2-dimethoxyethyl)-3-(4-fluorophenethyl)ureido)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide as an oil in 19% yield (0.19 g): MS (ES+) m/z 502.4 (M+1).

Workup

  1. customThe resulting reaction mixture
  2. waitThe reaction mixture was stired for 17 hour at ambient temperature
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by column chromatography
  5. washeluted with dichloromethane/methanol (4/1)

Sources & evidence

ORD record
ord-819e1316bdbb46a78de9d4b8a8d52010
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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