Sodium hydride → HCID 19418784, compound

HRID 864866Notes

Reaction equation

N1C=CC([CH:7]2[CH2:12][NH:11][CH2:10][CH2:9][N:8]2[C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)=CC=1.[H-].[Na+].Cl[C:23]1[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][N:24]=1>CN(C=O)C>[N:24]1[CH:25]=[CH:26][C:31]([N:11]2[CH2:12][CH2:7][N:8]([C:13]3[CH:14]=[CH:15][C:16]([O:19][C:23]4[N:24]=[CH:25][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:31][CH:32]=4)=[CH:17][CH:18]=3)[CH2:9][CH2:10]2)=[CH:32][CH:23]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of 4-((4-pyridyl)piperazin-1-yl)phenol (1.13 g) in DMF (10 ml) was added a 60% dispersion of sodium hydride in oil (195 mg) and the resulting mixture was stirred for 20 minutes. A solution of methyl 6-chloronicotinate (758 mg) in DMF (2 ml) was added and the mixture was heated at 60° C. for 2 hours. The mixture was partitioned between ethyl acetate(100 ml) and water(20 ml). The organic layer was dried (MgSO4) and evaporated to give an oil which was purified by flash column chromatography on silica, eluting with methanol/dichloromethane (5:95 v/v) to give the title compound as a solid (815 mg): mp 143°-144° C. ; NMR (d6DMSO) δ3.2-3.35 (4H,m) 3.45-3.55 (4H,m), 3.85 (3H,s), 6.9 (2H,dd), 7.05-7.1 (4H,m), 8.15-8.3 (3H,m), 8.7 (2H,d); m/e 391 (M+H)+ ; calculated for C22H22N4O3.0.25H2O: C,66.9; H,5.7; N,14.2. Found: C,66.9; H,5.7; N,14.1%.

Workup

customThe mixture was partitioned between ethyl acetate(100 ml) and water(20 ml)
dry with materialThe organic layer was dried (MgSO4)
customevaporated
customto give an oil which
customwas purified by flash column chromatography on silica
washeluting with methanol/dichloromethane (5:95 v/v)

Sources & evidence

ORD record: ord-41e43e75e4a34bedbd1f4ae03a8cc68f
Source dataset: uspto-grants-1996_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05563141

Reaction notes

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