Cyclopentylamine → 6-Cyclopropyl-3-(pyrimidin-5-ylamino)-pyridine-2-carboxylic acid (3-cyclopentylcarbamoyl-1-methyl-1H-pyrazol-4-yl)-amide

HRID 467657Notes

Reaction equation

[CH:1]1([NH2:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.C[O:8][C:9]([C:11]1[C:15]([NH:16][C:17]([C:19]2[C:24]([NH:25][C:26]3[CH:27]=[N:28][CH:29]=[N:30][CH:31]=3)=[CH:23][CH:22]=[C:21]([CH:32]3[CH2:34][CH2:33]3)[N:20]=2)=[O:18])=[CH:14][N:13]([CH3:35])[N:12]=1)=O>>[CH:1]1([NH:6][C:9]([C:11]2[C:15]([NH:16][C:17]([C:19]3[C:24]([NH:25][C:26]4[CH:27]=[N:28][CH:29]=[N:30][CH:31]=4)=[CH:23][CH:22]=[C:21]([CH:32]4[CH2:34][CH2:33]4)[N:20]=3)=[O:18])=[CH:14][N:13]([CH3:35])[N:12]=2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Reactant 2

HCID 2906Cyclopentylamine

HCID 700992004-{[6-Cyclopropyl-3-(pyrimidin-5-ylamino)-pyridine-2-carbonyl]-amino}-1-methyl-1H-pyrazole-3-carboxylic acid methyl ester

Product 1

HCID 701143536-Cyclopropyl-3-(pyrimidin-5-ylamino)-pyridine-2-carboxylic acid (3-cyclopentylcarbamoyl-1-methyl-1H-pyrazol-4-yl)-amideYield 19%

Procedure

According to the general method described in step 5 of example 27, reaction of cyclopentylamine with 4-{[6-cyclopropyl-3-(pyrimidin-5-ylamino)-pyridine-2-carbonyl]-amino}-1-methyl-1H-pyrazole-3-carboxylic acid methyl ester provided the title compound (19%) as amorphous yellow solid.

Sources & evidence

ORD record: ord-7c2bfa718e1d4512a5d8d66db698bd4e
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08623866B2

Reaction notes

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