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Dimethylformamide → HCID 68579999, compound

HRID 644306
Notes
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Reaction equation

HRID 644306 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 110425973-(Piperidin-4-yl)-3,4-dihydroquinazolin-2(1H)-oneHCID 22184541HCID 22184541, compound

Product 1

HCID 68579999HCID 68579999, compound

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

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

  1. stirringthe mixture was stirred for a further 30 min
  2. temperaturethe suspension was refluxed for 10 h
  3. customThe reaction mixture was evaporated down in vacuo
  4. extractionexhaustively extracted with EtOAc
  5. dry with materialdried over MgSO4
  6. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes