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

HRID 467753Notes

Reaction equation

HRID 467753 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[N:9]=[C:8]([C:10]([OH:12])=O)[C:7]([NH:13][C:14]2[CH:15]=[N:16][CH:17]=[N:18][CH:19]=2)=[CH:6][CH:5]=1.[CH3:20][NH:21][C:22]([C:24]1[N:25]([CH3:30])[N:26]=[CH:27][C:28]=1[NH2:29])=[O:23]>>[CH3:30][N:25]1[C:24]([C:22](=[O:23])[NH:21][CH3:20])=[C:28]([NH:29][C:10]([C:8]2[C:7]([NH:13][C:14]3[CH:15]=[N:16][CH:17]=[N:18][CH:19]=3)=[CH:6][CH:5]=[C:4]([CH2:3][O:2][CH3:1])[N:9]=2)=[O:12])[CH:27]=[N:26]1

Participants

3

Reactant 2

HCID 64853704-amino-N,1-dimethyl-1H-pyrazole-5-carboxamideHCID 700974336-Methoxymethyl-3-(pyrimidin-5-ylamino)-pyridine-2-carboxylic acid

Product 1

HCID 547598366-Methoxymethyl-3-(pyrimidin-5-ylamino)-pyridine-2-carboxylic acid (1-methyl-5-methylcarbamoyl-1H-pyrazol-4-yl)-amide

Procedure

The product was obtained starting from 6-methoxymethyl-3-(pyrimidin-5-ylamino)-pyridine-2-carboxylic acid (30 mg, 0.12 mmol) and 4-amino-2-methyl-2H-pyrazole-3-carboxylic acid methylamide (23 mg, 0.15 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 (28 mg, 61%).

Workup

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

Sources & evidence

ORD record
ord-cfee8020adc841a8ace91a2992ab4a06
Source dataset
uspto-grants-2014_01
Patent number
US08623866B2

Reaction notes

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