4-amino-N,1-dimethyl-1H-pyrazole-5-carboxamide → 3-(Pyrimidin-5-ylamino)-6-pyrrolidin-1-yl-pyrazine-2-carboxylic acid (1-methyl-5-methylcarbamoyl-1H-pyrazol-4-yl)-amide

HRID 467784Notes

Reaction equation

HRID 467784 reaction equation
[N:1]1[CH:6]=[C:5]([NH:7][C:8]2[C:9]([C:19]([OH:21])=O)=[N:10][C:11]([N:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)=[CH:12][N:13]=2)[CH:4]=[N:3][CH:2]=1.[CH3:22][NH:23][C:24]([C:26]1[N:27]([CH3:32])[N:28]=[CH:29][C:30]=1[NH2:31])=[O:25]>>[CH3:32][N:27]1[C:26]([C:24](=[O:25])[NH:23][CH3:22])=[C:30]([NH:31][C:19]([C:9]2[C:8]([NH:7][C:5]3[CH:4]=[N:3][CH:2]=[N:1][CH:6]=3)=[N:13][CH:12]=[C:11]([N:14]3[CH2:15][CH2:16][CH2:17][CH2:18]3)[N:10]=2)=[O:21])[CH:29]=[N:28]1

Participants

3

Reactant 2

HCID 64853704-amino-N,1-dimethyl-1H-pyrazole-5-carboxamideHCID 700969473-(Pyrimidin-5-ylamino)-6-pyrrolidin-1-yl-pyrazine-2-carboxylic acid

Product 1

HCID 585481443-(Pyrimidin-5-ylamino)-6-pyrrolidin-1-yl-pyrazine-2-carboxylic acid (1-methyl-5-methylcarbamoyl-1H-pyrazol-4-yl)-amide

Procedure

The product was obtained starting from 3-(pyrimidin-5-ylamino)-6-pyrrolidin-1-yl-pyrazine-2-carboxylic acid (30 mg, 94 μmol) and 4-amino-2-methyl-2H-pyrazole-3-carboxylic acid methylamide (19 mg, 123 μmol) according to the method described in example 64, step 6 after purification by preparative HPLC using an acetonitrile/water gradient as yellow solid (10 mg, 26%).

Workup

  1. customThe product was obtained
  2. customafter purification by preparative HPLC

Sources & evidence

ORD record
ord-dc2b6115bd03458ebbf8270adab09aeb
Source dataset
uspto-grants-2014_01
Patent number
US08623866B2

Reaction notes

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