Hydrogen Peroxide → HCID 23155198, compound

HRID 1912863Notes

Reaction equation

[C:1]([C:3]1[C:8]2[N:9]=[CH:10][N:11]([C:12]3[CH:17]=[CH:16][C:15]([NH:18][C:19]([NH:21][C:22]4[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[C:24]([CH2:32][N:33]5[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]5)[CH:23]=4)=[O:20])=[CH:14][CH:13]=3)[C:7]=2[CH:6]=[CH:5][N:4]=1)#[N:2].OO.C(=O)([O-])[O-:43].[K+].[K+]>CS(C)=O>[CH3:39][N:36]1[CH2:35][CH2:34][N:33]([CH2:32][C:24]2[CH:23]=[C:22]([NH:21][C:19](=[O:20])[NH:18][C:15]3[CH:16]=[CH:17][C:12]([N:11]4[C:7]5[CH:6]=[CH:5][N:4]=[C:3]([C:1]([NH2:2])=[O:43])[C:8]=5[N:9]=[CH:10]4)=[CH:13][CH:14]=3)[CH:27]=[C:26]([C:28]([F:30])([F:29])[F:31])[CH:25]=2)[CH2:38][CH2:37]1

Participants

Conditions

Temperature: 50 °C

Procedure

In 1 mL of dimethyl sulfoxide, 40 mg (0.07 mmol) of 1-[4-(4-cyano-imidazo[4,5-c]pyridin-1-yl)phenyl]-3-[3-(4-methylpiperazin-1-ylmethyl)-5-(trifluoromethyl)phenyl]urea was dissolved, and 40 μL (0.35 mmol) of a 30% hydrogen peroxide aqueous solution and 21 mg (0.15 mmol) of potassium carbonate were added thereto and the mixture solution was stirred at 50° C. for one hour. The reaction solution was partitioned between ethyl acetate and water, and the organic layer was washed with water and a saturated sodium chloride solution in the order named and concentrated under reduced pressure. The crude product was purified by a silica gel column (dichloromethane:methanol=10:1) to obtain 19 mg (45%) of a target product as a white solid.

Workup

customThe reaction solution was partitioned between ethyl acetate and water
washthe organic layer was washed with water
concentrationconcentrated under reduced pressure
customThe crude product was purified by a silica gel column (dichloromethane:methanol=10:1)

Sources & evidence

ORD record: ord-6d46e81b19aa40b3970df9c96786cad2
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609656B2

Reaction notes

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