Sodium hydride → HCID 59511251, compound

HRID 1157826Notes

Reaction equation

[H-].[Na+].[C:3]1([C:9]2[C:13]([N:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]3)=[CH:12][NH:11][N:10]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl.Cl[CH2:29][CH2:30][N:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1>CN(C=O)C>[O:34]1[CH2:35][CH2:36][N:31]([CH2:30][CH2:29][N:11]2[CH:12]=[C:13]([N:14]3[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][CH2:19]3)[C:9]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)=[N:10]2)[CH2:32][CH2:33]1

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium hydride (0.1 g) was taken in dry DMF (2 ml) and a solution of tert-butyl 4-(3-phenyl-1H-pyrazol-4-yl)piperazine-1-carboxylate (0.5 g in 2 ml of DMF) was added slowly at 0° C. The reaction mixture was stirred for 30 min at 0° C. and a solution of 2-chloroethylmorpholine hydrochloride (0.3 g) in DMF (1 ml) was added very slowly. The reaction mixture was allowed to stir over night at room temperature. The reaction mixture was quenched with cold water (5 ml) and extracted with ethyl acetate (3×40 ml). Evaporation of solvent under reduced pressure gave crude product, which, was purified by column chromatography using ethyl acetate/hexane (2:8) as eluent to afford compound tert-butyl 4-(1-(2-morpholinoethyl)-3-phenyl-1H-pyrazol-4-yl)piperazine-1-carboxylate as pure solid product.

Workup

stirringto stir over night at room temperature
customThe reaction mixture was quenched with cold water (5 ml)
extractionextracted with ethyl acetate (3×40 ml)
customEvaporation of solvent under reduced pressure
customgave crude product, which
customwas purified by column chromatography

Sources & evidence

ORD record: ord-a116bdeb0a7848f98e189b335f9fe728
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07807676B2

Reaction notes

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