N,1-dimethylpyrrolidin-3-amine → 6-Cyclopropyl-3-(pyrimidin-5-ylamino)-pyrazine-2-carboxylic acid {1-methyl-5-[methyl-(1-methyl-pyrrolidin-3-yl)-carbamoyl]-1H-pyrazol-4-yl}-amide

HRID 2368370Notes

Reaction equation

HRID 2368370 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]([OH:21])=O)=[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.[CH3:29][NH:30][CH:31]1[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32]1>>[CH3:18][N:15]1[C:14]([C:19](=[O:21])[N:30]([CH3:29])[CH:31]2[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32]2)=[C:13]([NH:12][C:10]([C:8]2[C:7]([NH:22][C:23]3[CH:28]=[N:27][CH:26]=[N:25][CH:24]=3)=[N:6][CH:5]=[C:4]([CH:1]3[CH2:2][CH2:3]3)[N:9]=2)=[O:11])[CH:17]=[N:16]1

Participants

3

Reactant 2

HCID 2758520N,1-dimethylpyrrolidin-3-amineHCID 700980734-{[6-Cyclopropyl-3-(pyrimidin-5-ylamino)-pyrazine-2-carbonyl]-amino}-2-methyl-2H-pyrazole-3-carboxylic acid

Product 1

HCID 547622046-Cyclopropyl-3-(pyrimidin-5-ylamino)-pyrazine-2-carboxylic acid {1-methyl-5-[methyl-(1-methyl-pyrrolidin-3-yl)-carbamoyl]-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 (25 mg, 66 μmol; example 236, step 3) and N,1-dimethyl-pyrrolidin-3-ylamine (10 mg, 85 μmol) according to the method described in example 64, step 6 after purification by preparative HPLC using an acetonitrile/water gradient as yellow solid (12 mg, 35%).

Workup

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

Sources & evidence

ORD record
ord-863e34407d57428e979a881e6f35adcb
Source dataset
uspto-grants-2014_04
Patent number
US08703768B2

Reaction notes

Loading…