1-Methyl-3-aminopyrazole → HCID 73297040, compound

HRID 592407Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]2([C:19]([NH2:21])=[O:20])[CH2:18][CH2:17]2)[C:5]([Cl:22])=[CH:4][N:3]=1.[CH3:23][N:24]1[CH:28]=[CH:27][C:26]([NH2:29])=[N:25]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCOCC1.CCOCC>[Cl:22][C:5]1[C:6]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]2([C:19]([NH2:21])=[O:20])[CH2:18][CH2:17]2)=[N:7][C:2]([NH:29][C:26]2[CH:27]=[CH:28][N:24]([CH3:23])[N:25]=2)=[N:3][CH:4]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 1-(2-(2-(2,5-dichloropyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide A14 (0.100 g, 0.297 mmol), 1-methyl-1H-pyrazole-3-amine (0.058 g, 0.595 mmol) and p-toluenesulfonic acid monohydrate (0.006 g, 0.030 mmol) in 1,4-dioxane (2.0 mL) was stirred in a microwave reactor at 120° C. for 3 hours. The reaction mixture was adsorbed onto SiO2 and purified by column chromatography (Biotage Isolera, 24 g SiO2 cartridge, 0-5% MeOH in DCM) to give a gummy solid. The solid was suspended in a mixture of Et2O and petroleum benzine 40-60° C. (1:1) and sonicated for 10 minutes. The precipitate was isolated by vacuum filtration and dried to give the title compound 28 as a yellow solid (0.014 g, 12%). LCMS-D: rt 3.26 min; m/z 397 [M+H]+.

Workup

custompurified by column chromatography (Biotage Isolera, 24 g SiO2 cartridge, 0-5% MeOH in DCM)
customto give a gummy solid
customsonicated for 10 minutes
customThe precipitate was isolated by vacuum filtration
customdried

Sources & evidence

ORD record: ord-e09ae11b7d3047ff84c9e3361f433d1b
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238644B2

Reaction notes

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