Ethyl chloroformate → 5-tert-butyl 1-ethyl 3-amino-1H-thieno[2,3-c]pyrazole-1,5-dicarboxylate

HRID 448128

반응식

HRID 448128 반응식
[C:1](Cl)(=[O:5])[O:2][CH2:3][CH3:4].[NH2:7][C:8]1[C:9]2[CH:15]=[C:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[S:13][C:10]=2[NH:11][N:12]=1.C(N(C(C)C)CC)(C)C>O1CCCC1>[NH2:7][C:8]1[C:9]2[CH:15]=[C:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[S:13][C:10]=2[N:11]([C:1]([O:2][CH2:3][CH3:4])=[O:5])[N:12]=1

참가 물질

5

반응물 3

HCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 178450636tert-butyl 3-amino-1H-thieno[2,3-c]pyrazole-5-carboxylate

생성물 1

HCID 577372725-tert-butyl 1-ethyl 3-amino-1H-thieno[2,3-c]pyrazole-1,5-dicarboxylate수율 87.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of ethyl chlorocarbonate (4.90 mL, 51.7 mmol) in tetrahydrofuran (THF, 60 mL) was slowly added to a mixture of tert-butyl 3-amino-1H-thieno[2,3-c]pyrazole-5-carboxylate (12.0 g, 50.2 mmol) and diisopropylethylamine (DIEA, 51.5 mL, 301 mmol) in THF (300 mL), maintaining the temperature between −5 and −10° C. The reaction was kept at the same temperature for 5 minutes then allowed to reach room temperature. The obtained mixture was evaporated to dryness under vacuum and the residue extracted with ethyl acetate (AcOEt) and water. The organic layer was separated, dried over sodium sulfate and evaporated to dryness. The resulting raw material was triturated with diethyl ether to give 13.7 g of the title compound as a white solid.

후처리

  1. temperaturemaintaining the temperature between −5 and −10° C
  2. customto reach room temperature
  3. customThe obtained mixture was evaporated to dryness under vacuum
  4. extractionthe residue extracted with ethyl acetate (AcOEt) and water
  5. customThe organic layer was separated
  6. dry with materialdried over sodium sulfate
  7. customevaporated to dryness
  8. customThe resulting raw material was triturated with diethyl ether

출처 및 근거

ORD 기록
ord-8c28da037f4a46bdac1523c02562e0d1
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481584B2

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