3,5-Dimethylisoxazole-4-carbonyl Chloride → HCID 178488220, Verbindung

HRID 432408

Reaktionsgleichung

Reaktionsgleichung von HRID 432408
[CH3:1][C:2]1[C:6]([C:7](Cl)=[O:8])=[C:5]([CH3:10])[O:4][N:3]=1.[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:26]3[C:21](=[N:22][CH:23]=[N:24][C:25]=3[NH2:27])[N:20]([C@H:28]3[CH2:33][CH2:32][C@@H:31]([N:34]4[CH2:39][CH2:38][N:37]([CH3:40])[CH2:36][CH2:35]4)[CH2:30][CH2:29]3)[N:19]=2)=[CH:14][C:13]=1[O:41][CH3:42]>N1C=CC=CC=1>[NH2:27][C:25]1[N:24]=[CH:23][N:22]=[C:21]2[N:20]([C@H:28]3[CH2:33][CH2:32][C@@H:31]([N:34]4[CH2:35][CH2:36][N:37]([CH3:40])[CH2:38][CH2:39]4)[CH2:30][CH2:29]3)[N:19]=[C:18]([C:15]3[CH:16]=[CH:17][C:12]([NH:11][C:7]([C:6]4[C:2]([CH3:1])=[N:3][O:4][C:5]=4[CH3:10])=[O:8])=[C:13]([O:41][CH3:42])[CH:14]=3)[C:26]=12

Komponenten

4

Edukt 2

HCID 27362653,5-Dimethylisoxazole-4-carbonyl ChlorideHCID 178488197HCID 178488197, Verbindung

Produkt 1

HCID 178488220HCID 178488220, VerbindungAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

3,5-Dimethyl-4-isoxazolecarbonyl chloride (22 mg, 0.137 mmol) was added to a solution of cis-3-(4-amino-3-methoxyphenyl)-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (30 mg, 0.067 mmol) in pyridine (0.5 mL). After 5 hours, the solvent was evaporated and the residue was re-crystallized from DMSO to give cis-N4-(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxyphenyl)-3,5-dimethyl-4-isoxazolecarboxamide (33 mg, 87%). 1H NMR (DMSO-d6) δ 1.91 (m, 2H), 2.24 (m, 2H), 2.36 (m, 2H), 2.41 (s, 3H), 2.63 (s, 3H), 2.77 (m, 3H), 3.17 (s, 3H), 3.37 (bm, 8H), 3.95 (s, 3H), 4.95 (m, 1H), 7.37 (m, 2H), 8.17 (d, J=8.17, 1H), 8.30 (s, 1H), 9.26 (s, 1H). LC/MS (Micromass-Column: Pecosphere, C18, 3 um, 33×4.6 mm. Eluents: 0% B/A to 100% B/A in 4.5 min. (B: acetonitrile, A: 50 mM ammonia acetate buffer, pH 4.5), 3.5 mL/min.), MH+ =560.2, Rt=2.44 min.

Aufarbeitung

  1. customthe solvent was evaporated
  2. customthe residue was re-crystallized from DMSO

Quellen und Nachweise

ORD-Eintrag
ord-e6457c1ee6414fcab2838471e941fb56
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06660744B1

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