Sodium hydride → HCID 53689583, compound

HRID 441229Notes

Reaction equation

Cl[C:2]1[C:7]([NH:8][C:9](=[O:19])[C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[H-].[Na+].Cl.[CH3:23][N:24](C)[CH2:25][CH2:26][CH2:27]Cl>CN(C)C=O.C(OCC)(=O)C>[N+:16]([C:13]1[CH:14]=[CH:15][C:10]([C:9]([N:8]2[CH2:27][CH2:26][CH2:25][N:24]([CH3:23])[C:2]3[N:3]=[CH:4][CH:5]=[CH:6][C:7]2=3)=[O:19])=[CH:11][CH:12]=1)([O-:18])=[O:17]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-chloro-3-(4-nitrobenzoyl)aminopyridine (1.93 g) in N,N-dimethylformamide (13 ml) was added sodium hydride (60 % in oil, 585 mg) and the solution was stirred at 0° C. for ten minutes. 3-Dimethylaminopropyl chloride hydrochloride (1.16 g) was added to the solution and the mixture was stirred for 3 hours at 150° C. The solution was diluted with ethyl acetate and the solution was washed with successively with water, saturated aqueous sodium hydrogen carbonate and brine. The organic phase was dried over sodium sulfate and the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (80 g, ethyl acetate:n-hexane =1:3) to give 1-(4-nitrobenzoyl)-5-methyl-2,3,4,5-tetrahydropyrido [3,2 -b][1,4]diazepine (450 mg).

Workup

stirringthe mixture was stirred for 3 hours at 150° C
washthe solution was washed with successively with water, saturated aqueous sodium hydrogen carbonate and brine
dry with materialThe organic phase was dried over sodium sulfate
customthe solvent was evaporated in vacuo
customThe residue was purified by silica gel column chromatography (80 g, ethyl acetate:n-hexane =1:3)

Sources & evidence

ORD record: ord-97c68ba5c75d4a06bca9f18ce2fa0d41
Source dataset: uspto-grants-1996_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05521170

Reaction notes

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