p-Toluenesulfonic acid → HCID 73296871, compound

HRID 592401Notes

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[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.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[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[N:3][CH:4]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A solution of 1-(2-(2-(2,5-dichloropyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide A14 (0.080 g, 0.24 mmol) in 1,4-dioxane (1.0 mL) containing aniline (0.043 mL, 0.48 mmol) and p-toluenesulfonic acid (4.5 mg, 0.024 mmol) was heated under microwave irradiation at 120° C. for 4 hours. The reaction mixture was adsorbed onto silica gel and purified by silica column chromatography (Combiflash Rf, 12 g SiO2 Cartridge, 20-50% EtOAc in cyclohexane) to give the title product 23 as a light yellow foam (0.044 g, 46%). LCMS-B: rt 7.718 min; m/z 393 [M+H]+.

Workup

custompurified by silica column chromatography (Combiflash Rf, 12 g SiO2 Cartridge, 20-50% EtOAc in cyclohexane)

Sources & evidence

ORD record: ord-7ea9b2cd1c234f21a168509d3fa666b2
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238644B2

Reaction notes

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