Hydrochloric Acid → 7-(4-Chlorophenyl)-2-(1,1-difluoroethyl)-8-isopropyl-3H-chromeno[7,8-d]imidazol-6-one

HRID 14493

Reaction equation

[NH2:1][C:2]1[C:11]([NH2:12])=[C:10]2[C:5]([C:6](=[O:23])[C:7]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)=[C:8]([CH:13]([CH3:15])[CH3:14])[O:9]2)=[CH:4][CH:3]=1.Cl.CCCCCC.C(OCC)C.[F:36][C:37]([F:42])([CH3:41])[C:38](O)=O>O>[Cl:22][C:19]1[CH:18]=[CH:17][C:16]([C:7]2[C:6](=[O:23])[C:5]3[CH:4]=[CH:3][C:2]4[NH:1][C:38]([C:37]([F:42])([F:36])[CH3:41])=[N:12][C:11]=4[C:10]=3[O:9][C:8]=2[CH:13]([CH3:14])[CH3:15])=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 110 °C

Procedure

7,8-Diamino-3-(4-chlorophenyl)-2-isopropyl-chromen-4-one (168 mg, 0.511 mmol) is dissolved in 2,2-difluoropropionic acid (562 mg), dilute hydrochloric acid (2M, 0.1 ml) is added, and the mixture is heated at 110° C. for 4 h. The reaction mixture is cooled to room temperature, diluted with water (10 ml) and extracted with ethyl acetate (3×30 ml). The ethyl acetate extracts are combined and washed with saturated sodium bicarbonate solution (2×40 ml) and saturated brine (40 ml). The organic layer is dried (MgSO4), treated with decolourising charcoal (50 mg), filtered and evaporated to give a colourless solid. This is sonicated with n-hexane/diethyl ether and filtered to give a cream-coloured powder.

Workup

temperatureThe reaction mixture is cooled to room temperature
extractionextracted with ethyl acetate (3×30 ml)
washwashed with saturated sodium bicarbonate solution (2×40 ml) and saturated brine (40 ml)
dry with materialThe organic layer is dried (MgSO4)
additiontreated with decolourising charcoal (50 mg)
filtrationfiltered
customevaporated
customto give a colourless solid
filtrationfiltered
customto give a cream-coloured powder

Sources & evidence

ORD record: ord-d6165b4813bc4d9eaebe17dccc6b897e
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732435B2

Linked notes

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