Dimethyl Sulfoxide → 1-{4-[8-(1-methyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-2-ylamino]-phenyl}-cyclopropanecarboxylic acid amide

HRID 2273009Notes

Reaction equation

HRID 2273009 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[C:8]3[N:9]([N:13]=[C:14]([NH:16][C:17]4[CH:22]=[CH:21][C:20]([C:23]5([C:26]#[N:27])[CH2:25][CH2:24]5)=[CH:19][CH:18]=4)[N:15]=3)[CH:10]=[CH:11][N:12]=2)[CH:4]=[N:3]1.C(=O)([O-])[O-:29].[K+].[K+].CS(C)=O>CO>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[C:8]3[N:9]([N:13]=[C:14]([NH:16][C:17]4[CH:22]=[CH:21][C:20]([C:23]5([C:26]([NH2:27])=[O:29])[CH2:25][CH2:24]5)=[CH:19][CH:18]=4)[N:15]=3)[CH:10]=[CH:11][N:12]=2)[CH:4]=[N:3]1

Participants

5

Reactant 3

HCID 679Dimethyl Sulfoxide2×HCID 11430Potassium CarbonateHCID 897671171-{4-[8-(1-methyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-2-ylamino]-phenyl}-cyclopropanecarbonitrile

Product 1

HCID 897687871-{4-[8-(1-methyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-2-ylamino]-phenyl}-cyclopropanecarboxylic acid amide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-{4-[8-(1-Methyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-2-ylamino]-phenyl}-cyclopropanecarbonitrile is dissolved in methanol before potassiumcarbonate (5 eq.), DMSO (3.5 eq) and hydrogeneperoxide (30% solution, 5.eq) are added. The mixture is stirred for 5 h and monitored via LCMS MS. DMSO (3.5 eq) and hydrogeneperoxide (30% solution, 5.eq) ares added and the mixture iss stirred at rt for 16 h. The mixture is concentrated and the crude material purified via column chromatographie. LCMS purity (Method D): 100%, Rt: 1.70 min, observed [M+H]=375.1;

Workup

  1. additionare added
  2. stirringthe mixture iss stirred at rt for 16 h
  3. concentrationThe mixture is concentrated
  4. customthe crude material purified via column chromatographie

Sources & evidence

ORD record
ord-6132e4915b904d8280a8c98b093f8cce
Source dataset
uspto-grants-2015_09
Patent number
US09120804B2

Reaction notes

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