1,1'-Carbonyldiimidazole → HCID 86645283, compound

HRID 560536Notes

Reaction equation

HRID 560536 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 86645283HCID 86645283, compoundYield 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-6a2162de4bfb492aa6cbd4c50f3af37c
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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