Hydrogen Peroxide → HCID 50944032, compound

HRID 1484886Notes

Reaction equation

HRID 1484886 reaction equation
[Cl:1][C:2]1[C:3]([NH:15][C:16]2[CH:20]=[C:19]([CH:21]3[CH2:23][CH2:22]3)[NH:18][N:17]=2)=[N:4][C:5]([C:8]2[S:12][C:11]([C:13]#[N:14])=[CH:10][CH:9]=2)=[N:6][CH:7]=1.OO.C([O-])([O-])=[O:27].[K+].[K+]>CS(C)=O>[Cl:1][C:2]1[C:3]([NH:15][C:16]2[CH:20]=[C:19]([CH:21]3[CH2:22][CH2:23]3)[NH:18][N:17]=2)=[N:4][C:5]([C:8]2[S:12][C:11]([C:13]([NH2:14])=[O:27])=[CH:10][CH:9]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 58169366HCID 58169366, compound2×

Product 1

HCID 50944032HCID 50944032, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 5-(5-chloro-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)thiophene-2-carbonitrile (Compound 140) (7 mg, 0.02 mmol, 1 equiv.), H2O2 (6.8 mg, 0.2 mmol, 10 equiv.) and K2CO3 (14 mg, 0.1 mmol, 5 equiv.) in DMSO (1 mL) was stirring at rt. for 1 h. The mixture was washed by water to afford 5-(5-chloro-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)thiophene-2-carboxamide (Compound 131) (5 mg, 69%). LC-MS (m/z)=361 [M+H]+; 1H NMR (400 MHz, DMSO-d6): δ 0.74 (d, J=14.4 Hz, 2H), 0.98 (d, J=7.6 Hz, 2H), 1.93-1.97 (m, 1H), 6.46 (s, 1H), 7.73-7.46 (m, 1H), 7.76 (s, 1H), 8.07-8.18 (m, 1H), 8.34 (d, J=12.8 Hz, 1H), 8.45 (d, J=6.4 Hz, 1H), 9.19-9.35 (m, 1H), 12.23-12.29 (m, 1H).

Workup

  1. washThe mixture was washed by water

Sources & evidence

ORD record
ord-220dc95dc7664346815848b513905de1
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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