Potassium Carbonate → (R)-benzyl-1-((5-carbamoyl-6-(3-(pyrimidin-2-yl)phenylamino)pyrazin-2-ylamino)(cyclopropyl)methyl)cyclopropylcarbamate

HRID 332819Notes

Reaction equation

HRID 332819 reaction equation
[CH2:1]([O:8][C:9](=[O:40])[NH:10][C:11]1([C@H:14]([NH:18][C:19]2[CH:24]=[N:23][C:22]([C:25]#[N:26])=[C:21]([NH:27][C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([C:34]4[N:39]=[CH:38][CH:37]=[CH:36][N:35]=4)[CH:29]=3)[N:20]=2)[CH:15]2[CH2:17][CH2:16]2)[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=[O:42].[K+].[K+]>CO.OO>[CH2:1]([O:8][C:9](=[O:40])[NH:10][C:11]1([C@H:14]([NH:18][C:19]2[CH:24]=[N:23][C:22]([C:25](=[O:42])[NH2:26])=[C:21]([NH:27][C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([C:34]4[N:39]=[CH:38][CH:37]=[CH:36][N:35]=4)[CH:29]=3)[N:20]=2)[CH:15]2[CH2:17][CH2:16]2)[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 86685609(R)-benzyl-1-((5-cyano-6-(3-(pyrimidin-2-yl)phenylamino)pyrazin-2-ylamino)(cyclopropyl)methyl)cyclopropylcarbamate

Product 1

HCID 86685611(R)-benzyl-1-((5-carbamoyl-6-(3-(pyrimidin-2-yl)phenylamino)pyrazin-2-ylamino)(cyclopropyl)methyl)cyclopropylcarbamate

Reagents, catalysts & solvents 2

HCID 784Hydrogen PeroxideCatalystHCID 887MethanolSolvent

Procedure

To a mixture of (R)-benzyl-1-((5-cyano-6-(3-(pyrimidin-2-yl)phenylamino)pyrazin-2-ylamino)(cyclopropyl)methyl)cyclopropylcarbamate in methanol (2 ml) was added K2CO3 (excess) and H2O2 (50%, a few drops). After completion, it was concentrated to give (R)-benzyl-1-((5-carbamoyl-6-(3-(pyrimidin-2-yl)phenylamino)pyrazin-2-ylamino)(cyclopropyl)methyl)cyclopropylcarbamate.

Workup

  1. concentrationAfter completion, it was concentrated

Sources & evidence

ORD record
ord-5a8d5d88f5a7475a8aa4296cd2e713e5
Source dataset
uspto-grants-2014_11
Patent number
US08877760B2

Reaction notes

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