Dimethylformamide → HCID 21911002, compound

HRID 1245329Notes

Reaction equation

HRID 1245329 reaction equation
CN(C=O)C.[CH2:6]([C:9]1[C:17]2[O:16][N:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[C:13]=2[CH:12]=[CH:11][C:10]=1[O:22][CH2:23][CH2:24][CH2:25][N:26]1[CH2:30][CH2:29][NH:28][C:27]1=[O:31])[CH2:7][CH3:8].[H-].[Na+].Br[CH:35]([CH3:40])[C:36]([O:38][CH3:39])=[O:37]>C(OCC)(=O)C>[O:31]=[C:27]1[N:26]([CH2:25][CH2:24][CH2:23][O:22][C:10]2[CH:11]=[CH:12][C:13]3[C:14]([C:18]([F:21])([F:19])[F:20])=[N:15][O:16][C:17]=3[C:9]=2[CH2:6][CH2:7][CH3:8])[CH2:30][CH2:29][N:28]1[CH:35]([CH3:40])[C:36]([O:38][CH3:39])=[O:37]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 95576Methyl 2-bromopropionateHCID 11726679HCID 11726679, compound

Product 1

HCID 21911002HCID 21911002, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a DMF solution (2 mL) of 1-(3-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}propyl)imidazolidin-2-one as prepared in Example 39 (10 mg, 0.027 mmol), was added NaH (4.3 mg, 1.08 mmol) and stirred at room temperature for 30 minutes. Methyl 2-bromopropionate (27 mg, 0.16 mmol) was added and the mixture stirred for another 3 hour. After aqueous work-up and silica gel chromatography (hexanes:70% ethyl acetate), the title compound was obtained.

Workup

  1. stirringthe mixture stirred for another 3 hour

Sources & evidence

ORD record
ord-073d55c7d74147e7aac0ebfaa57d0e48
Source dataset
uspto-grants-2006_10
Patent number
US07125865B2

Reaction notes

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