2-Chlorobenzoxazole → N-1,3-benzoxazol-2-yl-N'-(5-nitropyrimidin-4-yl)benzene-1,4-diamine

HRID 1429911Notes

Reaction equation

[N+:1]([C:4]1[C:5]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)=[N:6][CH:7]=[N:8][CH:9]=1)([O-:3])=[O:2].Cl[C:19]1[O:20][C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=1>CN1CCCC1=O.O>[O:20]1[C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=[C:19]1[NH:17][C:14]1[CH:15]=[CH:16][C:11]([NH:10][C:5]2[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=[CH:7][N:6]=2)=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of N-(5-nitropyrimidin-4-yl)benzene-1,4-diamine (256 mg), 2-chloro-1,3-benzoxazole (110 mg) in N-methylpyrrolidone (3 mL) was stirred at 120° C. for 45 min. After this time, the reaction mixture was cooled to ambient temperature, diluted with water (50 mL) and extracted with ethyl acetate (100 mL). The organic layer was washed with water (50 mL) then brine (50 mL), dried over sodium sulfate, and filtered and the filtrate was concentrated under reduced pressure. The residue obtained was purified by chromatography (silica, methylene chloride to 1:3 ethyl acetate/methylene chloride) to afford N-1,3-benzoxazol-2-yl-N′-(5-nitropyrimidin-4-yl)benzene-1,4-diamine (107 mg) as a red solid.

Workup

temperatureAfter this time, the reaction mixture was cooled to ambient temperature
extractionextracted with ethyl acetate (100 mL)
washThe organic layer was washed with water (50 mL)
dry with materialbrine (50 mL), dried over sodium sulfate
filtrationfiltered
concentrationthe filtrate was concentrated under reduced pressure
customThe residue obtained
customwas purified by chromatography (silica, methylene chloride to 1:3 ethyl acetate/methylene chloride)

Sources & evidence

ORD record: ord-deb6052dc69b48778ea4636c034755b2
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940758B2

Reaction notes

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