Dimethylformamide → HCID 21246144, compound

HRID 620374Notes

Reaction equation

[N:1]1[C:6]2[O:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[C:5]=2[CH:4]=[CH:3][N:2]=1.[H-].[Na+].[CH2:16]([CH:18]1[O:20][CH2:19]1)Br.[OH-].[Na+].CN(C)[CH:25]=[O:26]>O.CO>[O:20]1[CH2:19][CH:18]1[CH2:16][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:5]1[CH:4]=[CH:3][N:2]=[N:1][C:6]=1[O:26][CH3:25]

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirred solution of benzofuro[2,3-c]pyridazine (5.09 g) in dimethylformamide (40 ml) containing a suspension of sodium hydride (1.68 g, 50% oil) was added dry methanol (1.5 ml). The mixture was heated to 70° C. for 30 minutes and treated with epibromohydrin (10.2 ml) and stirring was continued at room temperature for 150 minutes. The mixture was poured into water (300 ml), taken to pH 10 with sodium hydroxide, extracted into dichloromethane and the organic extract was evaporated under reduced pressure to afford an oil that was purified by column chromatography (silica, chloroformpetrol, chloroform, chloroform-methanol) to afford 4-[2-(2,3-epoxypropoxy)phenyl]-3-methoxypyridazine as an oil. This was heated under reflux for 60 minutes with t-butylamine (20 ml) in methanol (50 ml) and the mixture was allowed to stand overnight. Evaporation under reduced pressure afford an oil which on treat ment with diethyl ether-petrol gave 4-(2-[3-t-butylamino-2-hydroxypropoxy)phenyl]-3-methoxypyridazine, m.p. 109.5°-110.5° C. from cyclohexane.

Workup

extractionextracted into dichloromethane
extractionthe organic extract
customwas evaporated under reduced pressure
customto afford an oil that
customwas purified by column chromatography (silica, chloroformpetrol, chloroform, chloroform-methanol)

Sources & evidence

ORD record: ord-985592f93122492990d7d1d373a4d00a
Source dataset: uspto-grants-1989_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04820819

Reaction notes

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