Sodium Cyanide → Ethyl 2-(3-(2-(4-fluorobenzylamino)-2-oxoethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate

HRID 1882364Notes

Reaction equation

HRID 1882364 reaction equation
C(O[C:4](=[O:23])[CH2:5][N:6]1[CH2:10][CH2:9][N:8]([C:11]2[S:12][C:13]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:14]([CH3:16])[N:15]=2)[C:7]1=[O:22])C.[F:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH2:30])=[CH:27][CH:26]=1.[C-]#N.[Na+]>ClCCl>[F:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH:30][C:4](=[O:23])[CH2:5][N:6]2[CH2:10][CH2:9][N:8]([C:11]3[S:12][C:13]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:14]([CH3:16])[N:15]=3)[C:7]2=[O:22])=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 673264-FluorobenzylamineHCID 57919757Ethyl 2-(3-(2-ethoxy-2-oxoethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate

Product 1

HCID 57919793Ethyl 2-(3-(2-(4-fluorobenzylamino)-2-oxoethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylateYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of ethyl 2-(3-(2-ethoxy-2-oxoethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate (0.43 g, 1.25 mmol), 4-fluorobenzylamine (3 mL) and catalytic amount of sodium cyanide was stirred at 80° C. for 16 h. The reaction mixture was allowed to cool to ambient temperature, diluted with dichloromethane (25 mL) and filtered. The solid was washed with dichloromethane and hexanes on the filter. The filtrate was filtered again, and the solid was washed with hexanes. The combined material was dried to afford the title compound as a colorless solid (0.45 g, 86%): 1H NMR (300 MHz, CDCl3) δ 7.28-7.20 (m, 2H), 7.05-6.97 (m, 2H), 6.42 (br s, 1H), 4.42 (d, J=5.7 Hz, 2H), 4.29 (q, J=7.1 Hz, 2H), 4.19-4.10 (m, 2H), 3.99 (s, 2H), 3.77-3.70 (m, 2H), 2.62 (s, 3H), 1.34 (t, J=7.1 Hz, 3H); MS (ES+) m/z 421.2 (M+1).

Workup

  1. temperatureto cool to ambient temperature
  2. filtrationfiltered
  3. washThe solid was washed with dichloromethane and hexanes on the filter
  4. filtrationThe filtrate was filtered again
  5. washthe solid was washed with hexanes
  6. customThe combined material was dried

Sources & evidence

ORD record
ord-a691abfff44b454cb867c03d16e2bdb2
Source dataset
uspto-grants-2012_11
Patent number
US08318949B2

Reaction notes

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