Dimethylformamide → HCID 68579999, compound

HRID 644306Notes

Reaction equation

C(N(C(C)C)C(C)C)C.[NH2:10][CH:11]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH3:24])=[C:19]([CH2:25][CH3:26])[CH:18]=1)[C:12]([O:14][CH3:15])=[O:13].[CH3:27][N:28]([CH:30]=[O:31])[CH3:29].N1C[CH2:36][CH:35]([N:38]2[CH2:47][C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[NH:40][C:39]2=[O:48])[CH2:34]C1>C1COCC1>[CH2:25]([C:19]1[CH:18]=[C:17]([CH2:16][CH:11]([NH:10][C:30]([N:28]2[CH2:29][CH2:34][CH:35]([N:38]3[CH2:47][C:46]4[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=4)[NH:40][C:39]3=[O:48])[CH2:36][CH2:27]2)=[O:31])[C:12]([O:14][CH3:15])=[O:13])[CH:22]=[CH:21][C:20]=1[CH2:23][CH3:24])[CH3:26]

Participants

Conditions

Temperature: 5 °C

Procedure

3.3 mL ethyldiisopropyl-amine and 2.06 g (12.6 mmol) of CDT were added to an ice-cooled solution of 2.95 g (12.54 mmol) of methyl 2-amino-3-(3,4-diethyl-phenyl)-propionate in 200 mL of THF and stirred for a further 90 min at 0-10° C. Then 20 mL of DMF were added, the mixture was stirred for a further 30 min, 2.91 g (12.6 mmol) of 3-piperidin-4-yl-3,4-dihydro-1H-quinazolin-2-one were added and the suspension was refluxed for 10 h. The reaction mixture was evaporated down in vacuo, combined with semisaturated NaHCO3 solution, exhaustively extracted with EtOAc and dried over MgSO4. After elimination of the desiccant and solvent the crude product was reacted without any further purification.

Workup

stirringthe mixture was stirred for a further 30 min
temperaturethe suspension was refluxed for 10 h
customThe reaction mixture was evaporated down in vacuo
extractionexhaustively extracted with EtOAc
dry with materialdried over MgSO4
customAfter elimination of the desiccant and solvent the crude product was reacted without any further purification

Sources & evidence

ORD record: ord-f7c9205a25b9464ea8c0a7531cf56ab5
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700589B2

Reaction notes

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