2-Nitrobenzoyl chloride → 3-(2-Nitro-benzoylamino)-furo[3,2-c]pyrazole-1,5-dicarboxylic acid 1-ethyl ester 5-propyl ester

HRID 1642333Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1642333
[CH2:1]([O:4][C:5]([C:7]1[O:14][C:13]2[C:12]([NH2:15])=[N:11][N:10]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:9]=2[CH:8]=1)=[O:6])[CH2:2][CH3:3].C(N(C(C)C)CC)(C)C.[N+:30]([C:33]1[CH:41]=[CH:40][CH:39]=[CH:38][C:34]=1[C:35](Cl)=[O:36])([O-:32])=[O:31]>O1CCCC1>[CH2:1]([O:4][C:5]([C:7]1[O:14][C:13]2[C:12]([NH:15][C:35](=[O:36])[C:34]3[CH:38]=[CH:39][CH:40]=[CH:41][C:33]=3[N+:30]([O-:32])=[O:31])=[N:11][N:10]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:9]=2[CH:8]=1)=[O:6])[CH2:2][CH3:3]

Komponenten

5

Edukt 3

HCID 118752-Nitrobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 426017253-Amino-furo[3,2-c]pyrazole-1,5-dicarboxylic acid 1-ethyl ester 5-propyl ester

Produkt 1

HCID 578786493-(2-Nitro-benzoylamino)-furo[3,2-c]pyrazole-1,5-dicarboxylic acid 1-ethyl ester 5-propyl esterAusbeute 74,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 3-amino-furo[3,2-c]pyrazole-1,5-dicarboxylic acid 1-ethyl ester 5-propyl ester (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-f46b149c0e424338a2a73f391a7309dc
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08119641B2

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