Water → HCID 10718461, compound

HRID 1288820Notes

Reaction equation

HRID 1288820 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[N:6][CH:5]=[N:4]1.Cl[CH2:9][C:10]1[N:15]=[C:14]2[S:16][C:17]([CH3:20])=[C:18]([CH3:19])[C:13]2=[C:12]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=2)[C:11]=1[C:31]([O:33][CH2:34][CH3:35])=[O:32].O>CN(C)C=O>[CH3:30][O:29][C:23]1[CH:22]=[C:21]([C:12]2[C:11]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[C:10]([CH2:9][N:3]3[CH:7]=[N:6][CH:5]=[N:4]3)[N:15]=[C:14]3[S:16][C:17]([CH3:20])=[C:18]([CH3:19])[C:13]=23)[CH:26]=[CH:25][C:24]=1[O:27][CH3:28]

Participants

6

Reactant 4

HCID 962WaterHCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 10812046HCID 10812046, compound

Product 1

HCID 10718461HCID 10718461, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% in oil, 0.171 g) was added to a solution of 1H-1,2,4-triazole (0.271 g) in N,N-dimethylformamide (DMF) (15 ml). The mixture was stirred for 15 minutes at room temperature, to which was added ethyl 6-chloromethyl-4-(3,4-dimethoxyphenyl)-2,3-dimethylthieno[2,3-b]pyridine-5-carboxylate (1.5 g). The mixture was stirred for 35 minutes at 80° C. The reaction mixture was poured into water, which was subjected to extraction with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4), then the solvent was distilled off. The residue was subjected to column chromatography on silica gel. From the fraction eluted with chloroform-methanol (30:1, v/v), ethyl 4-(3,4-dimethoxyphenyl)-2,3-dimethyl-6-(1,2,4-triazol-1-ylmethyl)thieno[2,3-b]pyridine-5-carboxylate (1.0 g, 62%) was obtained. Recrystallization from ethyl acetate-hexane gave colorless prisms, m.p.136°-137° C.

Workup

  1. stirringThe mixture was stirred for 35 minutes at 80° C
  2. extractionwas subjected to extraction with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried (MgSO4)
  5. distillationthe solvent was distilled off
  6. washFrom the fraction eluted with chloroform-methanol (30:1

Sources & evidence

ORD record
ord-f8bff13a703c412baa53e226e6d4e49f
Source dataset
uspto-grants-1998_05
Patent number
US05747486

Reaction notes

Loading…