Potassium Carbonate → (R)-N-cyclopropyl-4-methyl-3-(3-(1-(2-(oxiran-2-ylmethoxy)phenyl)cyclopropylamino)-2-oxopyrazin-1(2H)-yl)benzamide

HRID 1697384

Reaction equation

HRID 1697384 reaction equation
C(=O)([O-])[O-].[K+].[K+].[F-].[Cs+].[CH:9]1([NH:12][C:13](=[O:39])[C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[C:16]([N:21]3[CH:26]=[CH:25][N:24]=[C:23]([NH:27][C:28]4([C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=5[OH:37])[CH2:30][CH2:29]4)[C:22]3=[O:38])[CH:15]=2)[CH2:11][CH2:10]1.[N+](C1C=C(S(O[CH2:53][C@H:54]2[CH2:56][O:55]2)(=O)=O)C=CC=1)([O-])=O>CN(C=O)C>[CH:9]1([NH:12][C:13](=[O:39])[C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[C:16]([N:21]3[CH:26]=[CH:25][N:24]=[C:23]([NH:27][C:28]4([C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=5[O:37][CH2:53][C@H:54]5[CH2:56][O:55]5)[CH2:30][CH2:29]4)[C:22]3=[O:38])[CH:15]=2)[CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 25953Cesium fluorideHCID 146513Benzenesulfonic acid, 3-nitro-, (2R)-2-oxiranylmethyl esterHCID 66688774HCID 66688774, compound

Product 1

HCID 86663253(R)-N-cyclopropyl-4-methyl-3-(3-(1-(2-(oxiran-2-ylmethoxy)phenyl)cyclopropylamino)-2-oxopyrazin-1(2H)-yl)benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (216 mg) and cesium fluoride (36.5 mg) were added to N-cyclopropyl-3-(3-(1-(2-hydroxyphenyl)cyclopropylamino)-2-oxopyrazin-1(2H)-yl)-4-methylbenzamide (Example 167d, 500 mg) in DMF (9 mL) and stirred for 1 h. (R)-oxiran-2-ylmethyl 3-nitrobenzenesulfonate (311 mg) was added and the reaction stirred for 3 days. The reaction mixture was used without isolation/purification.

Workup

  1. additionwas added
  2. customThe reaction mixture was used without isolation/purification

Sources & evidence

ORD record
ord-ca876c2cc44e43f5a2f0ff6017a097f0
Source dataset
uspto-grants-2012_04
Patent number
US08163905B2

Linked notes

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