Phenyl chloroformate → 3-(3-Fluoro-phenylamino)-6,7-dimethoxy-4H-indeno[1,2-c]pyrazole-1-carboxylic acid phenyl ester

HRID 1714451Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1714451
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:21](=[CH:22][C:23]=1[O:24][CH3:25])[C:9]1=[N:10][NH:11][C:12]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=3)=[C:8]1[CH2:7]2.Cl[C:27]([O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:28].C(N(C(C)C)CC)(C)C>C1COCC1>[C:30]1([O:29][C:27]([N:10]2[C:9]3[C:21]4[C:6]([CH2:7][C:8]=3[C:12]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=3)=[N:11]2)=[CH:5][C:4]([O:3][CH3:2])=[C:23]([O:24][CH3:25])[CH:22]=4)=[O:28])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Komponenten

5

Edukt 3

HCID 15891Phenyl chloroformate2×HCID 81531DiisopropylethylamineHCID 178486504HCID 178486504, Verbindung2×

Produkt 1

HCID 588248603-(3-Fluoro-phenylamino)-6,7-dimethoxy-4H-indeno[1,2-c]pyrazole-1-carboxylic acid phenyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of (6,7-Dimethoxy-1,4-dihydro-indeno[1,2-c]pyrazol-3-yl)-(3-fluoro-phenyl)-amine (Compound 14) (1.5 g g, 4.2 mmol), phenyl chloroformate (Compound 55a) (0.76 mL, 6.3 mmole) and THF (10 mL) was added Diisopropylethylamine (DIPEA) (1.4 mL, 8.4 mmole) at room temperature with stirring. The reaction was stirred at room temperature over night. The reaction was quenched with saturated sodium bicarbonate and extracted with ethyl acetate. The solvent was dried over sodium sulfate and removed via rotovap to give a crude material (Compound 433). MS m/z 446.1 (M+H)+.

Aufarbeitung

  1. stirringThe reaction was stirred at room temperature over night
  2. customThe reaction was quenched with saturated sodium bicarbonate
  3. extractionextracted with ethyl acetate
  4. dry with materialThe solvent was dried over sodium sulfate
  5. customremoved via rotovap

Quellen und Nachweise

ORD-Eintrag
ord-f1da6daa6cb44229800a017a195f7702
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07795440B2

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