p-Toluenesulfonic acid monohydrate → HCID 178434559, compound

HRID 592404Notes

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.[NH2:23][C:24]1[C:25]([CH3:36])=[N:26][N:27](C(OC(C)(C)C)=O)[CH:28]=1.NC1C=NN(C(OC(C)(C)C)=O)C=1C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCOCC1>[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:23][C:24]2[C:25]([CH3:36])=[N:26][NH:27][CH:28]=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 (0.120 g, 0.357 mmol), tert-butyl 4-amino-3-methyl-1H-pyrazole-1-carboxylate or tert-butyl 4-amino-5-methyl-1H-pyrazole-1-carboxylate (isomer not determined) A26 (0.141 g, 0.714 mmol) and p-toluenesulfonic acid monohydrate (0.007 g, 0.04 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, 0-10% MeOH in DCM) to give the title compound 25 as a white solid (0.035 g, 25%). LCMS-A: rt 5.62 min; m/z 397 [M+H]+.

Workup

custompurified by column chromatography (Biotage Isolera, 24 g SiO2 cartridge, 0-10% MeOH in DCM)

Sources & evidence

ORD record: ord-63abd35a90d44316b84e23be7270e9b9
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238644B2

Reaction notes

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