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

Reaktionsgleichung

Reaktionsgleichung von HRID 549429
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 577372653-(2-Nitro-benzoylamino)-thieno[2,3-c]pyrazole-1,5-dicarboxylic Acid 5-tert-butyl Ester 1-ethyl EsterAusbeute 69,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-3a9d4cf274c4427fa0a0dc9f7027a263
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07943654B2

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