N-methyl-2-pyrrolidone → HCID 67388631, Verbindung

HRID 905694Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 905694
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[CH:10]=2)[C:5]([C:16]([NH2:18])=[O:17])=[CH:4][N:3]=1.[NH2:19][C:20]1[CH:42]=[CH:41][C:23]([CH2:24][N:25]([CH2:33][CH2:34][N:35]2[CH2:40][CH2:39][O:38][CH2:37][CH2:36]2)C(=O)OC(C)(C)C)=[CH:22][CH:21]=1.C(N(C(C)C)CC)(C)C.CN1C(=O)CCC1>O>[ClH:1].[ClH:1].[ClH:1].[CH3:15][C:11]1[CH:10]=[C:9]([NH:8][C:6]2[C:5]([C:16]([NH2:18])=[O:17])=[CH:4][N:3]=[C:2]([NH:19][C:20]3[CH:42]=[CH:41][C:23]([CH2:24][NH:25][CH2:33][CH2:34][N:35]4[CH2:36][CH2:37][O:38][CH2:39][CH2:40]4)=[CH:22][CH:21]=3)[N:7]=2)[CH:14]=[CH:13][CH:12]=1

Komponenten

6

Edukt 4

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 184608435-Pyrimidinecarboxamide, 2-chloro-4-[(3-methylphenyl)amino]-HCID 67387804Carbamic acid, [(4-aminophenyl)methyl][2-(4-morpholinyl)ethyl]-, 1,1-dimethylethyl ester

Produkt 1

HCID 67388631HCID 67388631, VerbindungAusbeute 70,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A mixture of 1.0 g of 2-chloro-4-(3-methylanilino)pyrimidine-5-carboxamide, 1.6 g of tert-butyl 4-aminobenzyl(2-morpholin-4-ylethyl)carbamate, 1.33 ml of diisopropylethylamine and 10 ml of NMP was stirred overnight at 130° C. The reaction mixture was cooled down to room temperature, and then mixed with water and extracted with ethyl acetate. The organic layer was washed with saturated brine, the solvent was evaporated, and the resulting residue was purified by a silica gel column chromatography (chloroform:methanol). Then, a 750 mg portion of 780 mg of the resulting compound was stirred overnight at room temperature in a mixed solution of 75 ml methanol and 30 ml 6 M hydrochloric acid. The reaction mixture was concentrated, and then the resulting crystals were washed with methanol to obtain 510 mg of 4-[(3-methylphenyl)amino]-2-[(4-{[(2-morpholin-4-ylethyl)amino]methyl}phenyl)amino]pyrimidine-5-carboxamide trihydrochloride as colorless crystals.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. customthe solvent was evaporated
  5. customthe resulting residue was purified by a silica gel column chromatography (chloroform:methanol)
  6. stirringThen, a 750 mg portion of 780 mg of the resulting compound was stirred overnight at room temperature in a mixed solution of 75 ml methanol and 30 ml 6 M hydrochloric acid
  7. concentrationThe reaction mixture was concentrated
  8. washthe resulting crystals were washed with methanol

Quellen und Nachweise

ORD-Eintrag
ord-e78bcd652d0344888d2c7663434997c6
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08012959B2

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