Water → 2-(2-(2-(5-Chloro-2-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-ylamino)pyrimidin-4-yl)ethyl)phenyl)propanamide

HRID 592426Notes

Reaction equation

[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([N:8]2[CH:12]=[C:11]([NH2:13])[CH:10]=[N:9]2)[CH2:4][CH2:3]1.Cl[C:15]1[N:20]=[C:19]([CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH:29]([CH3:33])[C:30]([NH2:32])=[O:31])[C:18]([Cl:34])=[CH:17][N:16]=1.O>CO>[Cl:34][C:18]1[C:19]([CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH:29]([CH3:33])[C:30]([NH2:32])=[O:31])=[N:20][C:15]([NH:13][C:11]2[CH:10]=[N:9][N:8]([CH:5]3[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]3)[CH:12]=2)=[N:16][CH:17]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A stirred solution of 1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-amine (0.117 g, 0.648 mmol), 2-(2-(2-(2,5-dichloropyrimidin-4-yl)ethyl)phenyl)propanamide A30 (0.060 g, 0.185 mmol) in MeOH (10 mL) and water (1.0 mL) was stirred at 70° C. for 16 hours. Additional 1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-amine (0.052 g, 0.29 mmol) was added and the reaction was stirred for 16 hours at 70° C. After cooling the solvent was removed to afford an oil which was purified by HPLC (Gradient: 30-100%, acetonitrile 0.1% formic acid in water 0.1% formic acid, 12 min) to give the title compound 44 as a red gum (0.0018 g, 2% yield). LCMS-C: rt 4.28 min; m/z 468 [M+H]+.

Workup

temperatureAfter cooling the solvent
customwas removed
customto afford an oil which
customwas purified by HPLC (Gradient: 30-100%, acetonitrile 0.1% formic acid in water 0.1% formic acid, 12 min)

Sources & evidence

ORD record: ord-4c5d21e20e5f4cf9aba184803ab63ad9
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238644B2

Reaction notes

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