Dimethyl Sulfoxide → HCID 67454394, compound

HRID 2276787Notes

Reaction equation

HRID 2276787 reaction equation
[F:1][CH:2]([F:27])[O:3][C:4]1[C:5]([C:10]([NH:13][C:14]2[N:15]=[N:16][C:17]([C:20]3[S:21][C:22]([C:25]#[N:26])=[CH:23][N:24]=3)=[CH:18][N:19]=2)([CH3:12])[CH3:11])=[N:6][CH:7]=[CH:8][CH:9]=1.C([O-])([O-])=[O:29].[K+].[K+].CS(C)=O.OO>C(O)(=O)C>[F:27][CH:2]([F:1])[O:3][C:4]1[C:5]([C:10]([NH:13][C:14]2[N:15]=[N:16][C:17]([C:20]3[S:21][C:22]([C:25]([NH2:26])=[O:29])=[CH:23][N:24]=3)=[CH:18][N:19]=2)([CH3:12])[CH3:11])=[N:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 67453746HCID 67453746, compound

Product 1

HCID 67454394HCID 67454394, compoundYield 148.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

2-(3-(2-(3-(difluoromethoxy)pyridin-2-yl)propan-2-ylamino)-1,2,4-triazin-6-yl)thiazole-5-carbonitrile (15 mg, 38 μmol), K2CO3 (50 mg, 0.35 mmol), and DMSO (1 mL) were combined in a vial and cooled to 0° C. H2O2 (0.1 mL of 35% solution) was then added and the reaction was warmed to rt and stirred for 1 h. Acetic acid (0.1 mL) was added, and the reaction was filtered and then purified using reverse phase chromatography to afford 23 mg of 2-(3-(2-(3-(difluoromethoxy)pyridin-2-yl)propan-2-ylamino)-1,2,4-triazin-6-yl)thiazole-5-carboxamide as a white solid, m/z=408.3 [M+H].

Workup

  1. temperaturethe reaction was warmed to rt
  2. filtrationthe reaction was filtered
  3. custompurified

Sources & evidence

ORD record
ord-b73f03f893b044908227f3790e5b4572
Source dataset
uspto-grants-2015_09
Patent number
US09133123B2

Reaction notes

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