Hydrogen Peroxide → HCID 89446854, compound

HRID 632732Notes

Reaction equation

HRID 632732 reaction equation
OO.[NH2:3][C:4]1([CH2:18][NH:19][C:20](=[O:29])[C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=2[F:28])[CH2:8][CH2:7][N:6]([C:9]2[C:14]([C:15]#[N:16])=[C:13]([NH2:17])[N:12]=[CH:11][N:10]=2)[CH2:5]1.C(=O)([O-])[O-:31].[K+].[K+]>CS(C)=O>[NH2:17][C:13]1[C:14]([C:15]([NH2:16])=[O:31])=[C:9]([N:6]2[CH2:7][CH2:8][C:4]([NH2:3])([CH2:18][NH:19][C:20](=[O:29])[C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=3[F:28])[CH2:5]2)[N:10]=[CH:11][N:12]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 89442615N-{[3-amino-1-(6-amino-5-cyanopyrimidin-4-yl)pyrrolidin-3-yl]methyl}-2,4-difluorobenzamide

Product 1

HCID 89446854HCID 89446854, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
40 °C

Procedure

Hydrogen peroxide (0.38 ml; 4.29 mmol; 40.0 eq.) was added dropwise to the mixture of N-{[3-amino-1-(6-amino-5-cyanopyrimidin-4-yl)pyrrolidin-3-yl]methyl}-2,4-difluorobenzamide (40.0 mg; 0.11 mmol; 1.0 eq.) and potassium carbonate (118.45 mg; 0.86 mmol; 8.0 eq.) in DMSO (3.0 ml) at room temperature. The resulting mixture was then stirred at 40° C. for 2 hours. The reaction mixture was workup and the crude was purified by reverse phase chromatography (Yamazen, acetonitrile/0.1% NH4OH in water) to yield the title compound in 40% yield. LC-MS: (M+1=392, obsd.=392).

Workup

  1. customthe crude was purified by reverse phase chromatography (Yamazen, acetonitrile/0.1% NH4OH in water)

Sources & evidence

ORD record
ord-a91518f907b4410f90522ccce667aa71
Source dataset
uspto-grants-2016_04
Patent number
US09321760B2

Reaction notes

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