Diethyl Ether → 4-{[(1S,2R)-2-aminocyclohexyl]amino}-N-(2-methoxyethyl)-6-methylquinazolin-2-carboxamide

HRID 75525Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 75525
[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6]([C:8]1[N:17]=[C:16]([NH:18][C@H:19]2[CH2:24][CH2:23][CH2:22][CH2:21][C@H:20]2[NH:25]C(=O)OC(C)(C)C)[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH3:33])[CH:14]=2)[N:9]=1)=[O:7].C(OCC)(=O)C.Cl.C(OCC)C>C(OCC)(=O)C>[NH2:25][C@@H:20]1[CH2:21][CH2:22][CH2:23][CH2:24][C@@H:19]1[NH:18][C:16]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH3:33])[CH:14]=2)[N:9]=[C:8]([C:6]([NH:5][CH2:4][CH2:3][O:2][CH3:1])=[O:7])[N:17]=1

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 21866389Hydrogen chloride-ethyl acetateHCID 86638400tert-butyl {(1R,2S)-2-[(2-{[(2-methoxyethyl)amino]carbonyl}-6-methylquinazolin-4-yl)amino]cyclohexyl}carbamate

Produkt 1

HCID 687002114-{[(1S,2R)-2-aminocyclohexyl]amino}-N-(2-methoxyethyl)-6-methylquinazolin-2-carboxamideAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a suspension of 2.24 g of tert-butyl {(1R,2S)-2-[(2-{[(2-methoxyethyl)amino]carbonyl}-6-methylquinazolin-4-yl)amino]cyclohexyl}carbamate in 10 ml of ethyl acetate, 10 ml of a 4 N hydrogen chloride-ethyl acetate solution was added, and the mixture was stirred at room temperature for 48 hours. To the reaction solution, 20 ml of diethyl ether was added, and the mixture was stirred for 30 minutes. Then, the deposited substance was collected by filtration, washed with diethyl ether and dried under reduced pressure. The resulting powder was purified by Fuji Silysia NH silica gel column chromatography (chloroform:methanol=20:1), whereby 1.61 g of a desired compound was obtained as a colorless powder.

Aufarbeitung

  1. additionwas added
  2. stirringthe mixture was stirred for 30 minutes
  3. filtrationThen, the deposited substance was collected by filtration
  4. washwashed with diethyl ether
  5. customdried under reduced pressure
  6. customThe resulting powder was purified by Fuji Silysia NH silica gel column chromatography (chloroform:methanol=20:1)

Quellen und Nachweise

ORD-Eintrag
ord-ccbe36490b6e44f4b12ab1b7f4b8d921
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835446B2

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