1-Methylazetidin-3-amine dihydrochloride → 6-Cyclopropyl-3-(pyrimidin-5-ylamino)-pyrazine-2-carboxylic acid [1-methyl-5-(1-methyl-azetidin-3-ylcarbamoyl)-1H-pyrazol-4-yl]-amide

HRID 467785

Reaction equation

HRID 467785 reaction equation
[CH:1]1([C:4]2[N:9]=[C:8]([C:10]([NH:12][C:13]3[CH:17]=[N:16][N:15]([CH3:18])[C:14]=3[C:19](O)=[O:20])=[O:11])[C:7]([NH:22][C:23]3[CH:24]=[N:25][CH:26]=[N:27][CH:28]=3)=[N:6][CH:5]=2)[CH2:3][CH2:2]1.Cl.Cl.[CH3:31][N:32]1[CH2:35][CH:34]([NH2:36])[CH2:33]1>>[CH3:18][N:15]1[C:14]([C:19](=[O:20])[NH:36][CH:34]2[CH2:35][N:32]([CH3:31])[CH2:33]2)=[C:13]([NH:12][C:10]([C:8]2[C:7]([NH:22][C:23]3[CH:24]=[N:25][CH:26]=[N:27][CH:28]=3)=[N:6][CH:5]=[C:4]([CH:1]3[CH2:3][CH2:2]3)[N:9]=2)=[O:11])[CH:17]=[N:16]1

Participants

3

Reactant 2

HCID 447849011-Methylazetidin-3-amine dihydrochlorideHCID 700980734-{[6-Cyclopropyl-3-(pyrimidin-5-ylamino)-pyrazine-2-carbonyl]-amino}-2-methyl-2H-pyrazole-3-carboxylic acid

Product 1

HCID 547609446-Cyclopropyl-3-(pyrimidin-5-ylamino)-pyrazine-2-carboxylic acid [1-methyl-5-(1-methyl-azetidin-3-ylcarbamoyl)-1H-pyrazol-4-yl]-amide

Procedure

The product was obtained starting from 4-{[6-cyclopropyl-3-(pyrimidin-5-ylamino)-pyrazine-2-carbonyl]-amino}-2-methyl-2H-pyrazole-3-carboxylic acid (30 mg, 79 μmol; example 236, step 3) and 1-methylazetidin-3-amine dihydrochloride (16 mg, 100 μmol) according to the method described in example 64, step 6 after purification by preparative HPLC using an acetonitrile/water gradient as yellow solid (11 mg, 31%).

Workup

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

Sources & evidence

ORD record
ord-62c52ecae7a44be19a3ad926a7b21654
Source dataset
uspto-grants-2014_01
Patent number
US08623866B2

Linked notes

Loading…