Diisopropyl Ether → tert-butyl {(1R,2S)-2-[(2-{[(2-methoxyethyl)amino]carbonyl}-6-methylquinazolin-4-yl)amino]cyclohexyl}carbamate

HRID 1971134Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]1[NH:15][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([CH3:26])[CH:24]=2)[N:19]=[C:18]([C:27]([O-:29])=O)[N:17]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:30][O:31][CH2:32][CH2:33][NH2:34].C(OC(C)C)(C)C>CO>[CH3:30][O:31][CH2:32][CH2:33][NH:34][C:27]([C:18]1[N:17]=[C:16]([NH:15][C@H:10]2[CH2:11][CH2:12][CH2:13][CH2:14][C@H:9]2[NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([CH3:26])[CH:24]=2)[N:19]=1)=[O:29]

Participants

Conditions

Temperature: 50 °C

Procedure

To a suspension of 15.0 g of ethyl 4-({(1S,2R)-2-[(tert-butoxycarbonyl)amino]cyclohexyl}amino-6-methylquinazolin-2-carboxylate in 15 ml of methanol, 7.89 g of 2-methoxyethylamine was added, and the mixture was stirred at 50° C. for 15 hours. After the reaction solution was cooled to room temperature, 45 ml of diisopropyl ether was added thereto, and the mixture was stirred at 0° C. for 30 minutes. The deposited crystal was collected by filtration, washed with diisopropyl ether and dried under reduced pressure, whereby 12.2 g of a desired compound was obtained as a white powder.

Workup

additionwas added
temperatureAfter the reaction solution was cooled to room temperature
stirringthe mixture was stirred at 0° C. for 30 minutes
filtrationThe deposited crystal was collected by filtration
washwashed with diisopropyl ether
customdried under reduced pressure

Sources & evidence

ORD record: ord-4985bb10eeab49bcbb37f3effa2a6f53
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431586B2

Reaction notes

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