4-amino-N,1-dimethyl-1H-pyrazole-5-carboxamide → 5-Bromo-2-cyclobutyl-pyrimidine-4-carboxylic acid (1-methyl-5-methylcarbamoyl-1H-pyrazol-4-yl)-amide

HRID 2368352Notes

Reaction equation

HRID 2368352 reaction equation
[Br:1][C:2]1[C:3]([C:12]([OH:14])=O)=[N:4][C:5]([CH:8]2[CH2:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1.[CH3:15][NH:16][C:17]([C:19]1[N:20]([CH3:25])[N:21]=[CH:22][C:23]=1[NH2:24])=[O:18]>>[CH3:25][N:20]1[C:19]([C:17](=[O:18])[NH:16][CH3:15])=[C:23]([NH:24][C:12]([C:3]2[C:2]([Br:1])=[CH:7][N:6]=[C:5]([CH:8]3[CH2:9][CH2:10][CH2:11]3)[N:4]=2)=[O:14])[CH:22]=[N:21]1

Participants

3

Reactant 2

HCID 64853704-amino-N,1-dimethyl-1H-pyrazole-5-carboxamideHCID 700971745-Bromo-2-cyclobutylpyrimidine-4-carboxylic acid

Product 1

HCID 866601965-Bromo-2-cyclobutyl-pyrimidine-4-carboxylic acid (1-methyl-5-methylcarbamoyl-1H-pyrazol-4-yl)-amide

Procedure

The product was obtained starting from 5-bromo-2-cyclobutyl-pyrimidine-4-carboxylic acid (37 mg, 0.14 mmol) and 4-amino-2-methyl-2H-pyrazole-3-carboxylic acid methylamide (29 mg, 0.19 mmol) according to the method described in example 64, step 6 after purification by preparative HPLC using an acetonitrile/water gradient as off-white solid (24 mg, 42%).

Workup

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

Sources & evidence

ORD record
ord-2d41d76350134634a2ec19913f13258c
Source dataset
uspto-grants-2014_04
Patent number
US08703768B2

Reaction notes

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