Methyl chloroformate → HCID 178501950, Verbindung

HRID 1865653Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1865653
Cl[C:2]([O:4][CH3:5])=[O:3].[NH2:6][C:7]1[CH:17]=[CH:16][C:15]([C:18]2[CH:19]=[C:20]3[C:26]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[O:33][CH3:34])=[N:25][NH:24][C:21]3=[N:22][CH:23]=2)=[CH:14][C:8]=1[C:9]([N:11]([CH3:13])[CH3:12])=[O:10]>ClCCl>[CH3:5][O:4][C:2](=[O:3])[NH:6][C:7]1[CH:17]=[CH:16][C:15]([C:18]2[CH:19]=[C:20]3[C:26]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[O:33][CH3:34])=[N:25][NH:24][C:21]3=[N:22][CH:23]=2)=[CH:14][C:8]=1[C:9](=[O:10])[N:11]([CH3:13])[CH3:12]

Komponenten

4

Edukt 2

HCID 6586Methyl chloroformateHCID 178489397HCID 178489397, Verbindung

Produkt 1

HCID 178501950HCID 178501950, VerbindungAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Methyl chloroformate (42 ul, 0.53 mmol) was added dropwise to a solution of 2-amino-5-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4,b]pyridin-5-yl]-N,N-dimethyl-benzamide (21 mg, 0.05 mmol) in dichloromethane/saturated aqueous sodium bicarbonate (1:1) at 0° C. The mixture was stirred for another 3 hours, allowing to slowly warm to room temperature. The reaction was washed three times with water (5 ml), dried over sodium sulfate and concentrated to dryness. The crude was purified by flash chromatography on silica gel using a gradient of ethyl acetate and hexane to afford {2-dimethylcarbamoyl-4[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-phenyl}-carbamic acid methyl ester (4.9 mg, 21% yield). 1H NMR (500 MHz, DMSO-d6) δ 2.88 (d, 6H), 3.58 (s, 3H), 3.77 (s, 3H), 7.03 (m, 1H), 7.15 (d, 1H), 7.40 (m, 1H), 7.58 (s, 1H), 7.64 (d, 1H), 7.73 (d, 1H), 8.27 (s, 1H), 8.78 (s, 1H), 9.03 (s, 1H), 13.75 (s, 1H); MS: m/z 446.1 (M+H+).

Aufarbeitung

  1. washThe reaction was washed three times with water (5 ml)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated to dryness
  4. customThe crude was purified by flash chromatography on silica gel using a gradient of ethyl acetate and hexane

Quellen und Nachweise

ORD-Eintrag
ord-15f164994c1b4ded8c3f593fae9485dd
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07626021B2

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