6-Cyclopropyl-3-(pyridin-3-ylamino)pyrazine-2-carboxylic acid → 6-Cyclopropyl-3-(pyridin-3-ylamino)-pyrazine-2-carboxylic acid [5-(azetidine-1-carbonyl)-1-methyl-1H-pyrazol-4-yl]-amide

HRID 467767Notes

Reaction equation

HRID 467767 reaction equation
[CH:1]1([C:4]2[N:9]=[C:8]([C:10]([OH:12])=O)[C:7]([NH:13][C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)=[N:6][CH:5]=2)[CH2:3][CH2:2]1.[NH2:20][C:21]1[CH:25]=[N:24][N:23]([CH3:26])[C:22]=1[C:27]([N:29]1[CH2:32][CH2:31][CH2:30]1)=[O:28]>>[N:29]1([C:27]([C:22]2[N:23]([CH3:26])[N:24]=[CH:25][C:21]=2[NH:20][C:10]([C:8]2[C:7]([NH:13][C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)=[N:6][CH:5]=[C:4]([CH:1]3[CH2:2][CH2:3]3)[N:9]=2)=[O:12])=[O:28])[CH2:30][CH2:31][CH2:32]1

Participants

3

Reactant 2

HCID 700965386-Cyclopropyl-3-(pyridin-3-ylamino)pyrazine-2-carboxylic acidHCID 70098437(4-Amino-2-methyl-2H-pyrazol-3-yl)-azetidin-1-yl-methanone

Product 1

HCID 585481686-Cyclopropyl-3-(pyridin-3-ylamino)-pyrazine-2-carboxylic acid [5-(azetidine-1-carbonyl)-1-methyl-1H-pyrazol-4-yl]-amide

Procedure

The product was obtained starting from 6-cyclopropyl-3-(pyridin-3-ylamino)pyrazine-2-carboxylic acid (30 mg, 0.12 mmol; example 217, step 2) and (4-amino-2-methyl-2H-pyrazol-3-yl)-azetidin-1-yl-methanone (27 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 light yellow solid (37 mg, 75%).

Workup

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

Sources & evidence

ORD record
ord-e58439ae78cf4a468f3f3130c2f507ff
Source dataset
uspto-grants-2014_01
Patent number
US08623866B2

Reaction notes

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