2-Nitrobenzoyl chloride → 3-(2-Nitro-benzoylamino)-thieno[2,3-c]pyrazole-1,5-dicarboxylic Acid 5-tert-butyl Ester 1-ethyl Ester

HRID 549429

반응식

HRID 549429 반응식
[NH2:1][C:2]1[C:3]2[CH:14]=[C:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[S:12][C:4]=2[N:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1.C(N(C(C)C)CC)(C)C.[N+:31]([C:34]1[CH:42]=[CH:41][CH:40]=[CH:39][C:35]=1[C:36](Cl)=[O:37])([O-:33])=[O:32]>O1CCCC1>[CH2:10]([O:9][C:7]([N:5]1[C:4]2[S:12][C:13]([C:15]([O:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[O:16])=[CH:14][C:3]=2[C:2]([NH:1][C:36](=[O:37])[C:35]2[CH:39]=[CH:40][CH:41]=[CH:42][C:34]=2[N+:31]([O-:33])=[O:32])=[N:6]1)=[O:8])[CH3:11]

참가 물질

5

반응물 3

HCID 118752-Nitrobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 577372725-tert-butyl 1-ethyl 3-amino-1H-thieno[2,3-c]pyrazole-1,5-dicarboxylate

생성물 1

HCID 577372653-(2-Nitro-benzoylamino)-thieno[2,3-c]pyrazole-1,5-dicarboxylic Acid 5-tert-butyl Ester 1-ethyl Ester수율 69.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 5-tert-butyl 1-ethyl 3-amino-1H-thieno[2,3-c]pyrazole-1,5-dicarboxylate (500 mg, 1.606 mmol) and diisopropylethylamine (DIEA, 0.824 mL, 4.818 mmol) in tetrahydrofuran (THF, 20 mL) at 0° C., 2-nitro-benzoyl chloride (0.318 mL, 2.409 mmol) was added. The reaction mixture was kept at the same temperature for 10 minutes then allowed to reach room temperature and let react overnight. The solvent was removed under vacuum, the residue was dissolved in dichloromethane (DCM) and washed with a 10% solution of acetic acid (AcOH), water, saturated NaHCO3 and brine. The crude was purified on silica gel (eluant dichloromethane/methanol 96/4) yielding 512 mg (69%) of the title compound.

후처리

  1. customto reach room temperature
  2. customlet react overnight
  3. customThe solvent was removed under vacuum
  4. dissolutionthe residue was dissolved in dichloromethane (DCM)
  5. washwashed with a 10% solution of acetic acid (AcOH), water, saturated NaHCO3 and brine
  6. customThe crude was purified on silica gel (eluant dichloromethane/methanol 96/4)

출처 및 근거

ORD 기록
ord-3a9d4cf274c4427fa0a0dc9f7027a263
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07943654B2

연결된 노트

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