Water → 2-{2-[2-Amino-4-(1,3-dihydroisoindole-2-carbonyl)quinazolin-6-yl]benzylamino}acetamide

HRID 1631123Notes

Reaction equation

[NH2:1][C:2]1[N:11]=[C:10]([C:12]([N:14]2[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15]2)=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:23]3[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=3C=O)[CH:8]=2)[N:3]=1.Cl.[NH2:32][CH2:33][C:34]([NH2:36])=[O:35].[C:37](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>ClCCCl.O1CCCC1>[NH2:1][C:2]1[N:11]=[C:10]([C:12]([N:14]2[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15]2)=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:23]3[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=3[CH2:37][NH:32][CH2:33][C:34]([NH2:36])=[O:35])[CH:8]=2)[N:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

100 mg of 2-[2-amino-4-(1,3-dihydroisoindole-2-carbonyl)quinazolin-6-yl]benzaldehyde are dissolved in 3 ml of 1,2-dichloroethane and 3 ml of tetrahydrofuran. 39 mg of aminoacetamide hydrochloride are added, and the mixture is stirred at 60° C. for 6 h. After cooling to 25° C., 113 mg of sodium triacetoxyborohydride are added and stirred at 25° C. for a further 12 h. The mixture is poured into water, extracted three times with dichloromethane, and the combined organic phases are dried over sodium sulfate. After filtration, the filtrate is evaporated to dryness and purified by chromatography (reversed phase HPLC).

Workup

temperatureAfter cooling to 25° C.
stirringstirred at 25° C. for a further 12 h
extractionextracted three times with dichloromethane
dry with materialthe combined organic phases are dried over sodium sulfate
filtrationAfter filtration
customthe filtrate is evaporated to dryness
custompurified by chromatography (reversed phase HPLC)

Sources & evidence

ORD record: ord-2c7586b32ab74fd2af71dee9a1bce016
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791129B2

Reaction notes

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