Triethylamine → Ethyl 1-(2-fluorobenzyl)-1H-imidazo[2,1-c][1,2,4]triazole-3-carboxylate

HRID 1640337노트

반응식

HRID 1640337 반응식
Cl/[C:2](=[N:8]\[NH:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[F:17])/[C:3]([O:5][CH2:6][CH3:7])=[O:4].C(S[C:22]1[NH:23][CH:24]=[CH:25][N:26]=1)C=C.C(N(CC)CC)C>O1CCOCC1>[F:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[CH2:10][N:9]1[C:22]2=[N:26][CH:25]=[CH:24][N:23]2[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[N:8]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 552877472-Allylsulfanyl-1H-imidazoleHCID 58142732ethyl (2Z)-2-chloro-2-[(2-fluorophenyl)methylhydrazinylidene]acetate

생성물 1

HCID 58142731Ethyl 1-(2-fluorobenzyl)-1H-imidazo[2,1-c][1,2,4]triazole-3-carboxylate

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

Ethyl (2Z)-chloro[(2-fluorobenzyl)hydrazono]acetate (750 mg, 2.90 mmol) from example 2A, 2-allylthio-1H-imidazole [U.S. Pat. No. 3,574,593; Chem. Abstr. 75, 49078] (1.20 g, 7.25 mmol) and triethylamine (293 mg, 2.90 mmol) are dissolved in dioxane (10 ml) and heated under reflux for 4 h. This is followed by dilution with water and extraction with ethyl acetate. The organic phase is dried over sodium sulfate, and the crude product is purified by chromatography on silica gel (eluent: dichloromethane/methanol 50:1). 410 mg (41% of theory) of the desired product are obtained with 84% purity.

후처리

  1. temperatureheated
  2. temperatureunder reflux for 4 h
  3. extractionThis is followed by dilution with water and extraction with ethyl acetate
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customthe crude product is purified by chromatography on silica gel (eluent: dichloromethane/methanol 50:1)

출처 및 근거

ORD 기록
ord-88ef207e309d442ca261c1b95463e627
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08114400B2

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