Sodium hydride → N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-[(E)-2-(1,3-thiazol-2-yl)vinyl]-1H-1,2,3-triazole-4-carboxamide

HRID 1717371Notes

Reaction equation

HRID 1717371 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[N:8]=[N:9][N:10]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([NH:29][CH2:30][CH3:31])=[O:28])=[CH:23][CH:22]=3)[C:11]=2[CH2:12]P(OCC)(OCC)=O)=[O:6])[CH2:3][CH2:2]1.[H-].[Na+].[CH:34]([C:36]1[S:37][CH:38]=[CH:39][N:40]=1)=O>C1COCC1>[CH:1]1([NH:4][C:5]([C:7]2[N:8]=[N:9][N:10]([C:21]3[CH:22]=[CH:23][C:24]([C:27]([NH:29][CH2:30][CH3:31])=[O:28])=[CH:25][CH:26]=3)[C:11]=2/[CH:12]=[CH:34]/[C:36]2[S:37][CH:38]=[CH:39][N:40]=2)=[O:6])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27349031,3-Thiazole-2-carbaldehydeHCID 86629812N-cyclopropyl-5-(diethylphosphonomethyl)-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxamide

Product 1

HCID 57664936N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-[(E)-2-(1,3-thiazol-2-yl)vinyl]-1H-1,2,3-triazole-4-carboxamideYield 48.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of N-cyclopropyl-5-(diethylphosphonomethyl)-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxamide (340 mg) obtained in Example 321b) in THF (5 ml) was added sodium hydride (50% oil dispersion, 55 mg) at 0° C., and the mixture was stirred at room temperature for 30 min. A solution of 2-formylthiazole (86 mg) in THF (1 ml) was added to the obtained reaction mixture, and the mixture was stirred at room temperature for 2 hr. The resultant precipitate was collected by filtration to give the title compound as a white solid (149 mg).

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hr
  2. filtrationThe resultant precipitate was collected by filtration

Sources & evidence

ORD record
ord-6aa358e93a9449c3ae31a38ab274e11f
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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