Dimethylformamide → HCID 21246144, compound

HRID 2118530Notes

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, chloroform-petrol, 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 treatment 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, chloroform-petrol, chloroform, chloroform-methanol)

Sources & evidence

ORD record: ord-ae344dc0dfea4761b3840e8e2d670ba1
Source dataset: uspto-grants-1987_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04678786

Reaction notes

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