2,4-Dichloro-7-methoxyquinoline → [1-(4-chloro-7-methoxy-quinolin-2-yl)-1H-pyrazol-3-yl]-isopropyl-amine

HRID 1965931Notes

Reaction equation

Cl[C:2]1[CH:11]=[C:10]([Cl:12])[C:9]2[C:4](=[CH:5][C:6]([O:13][CH3:14])=[CH:7][CH:8]=2)[N:3]=1.[CH:15]([NH:18][C:19]1[CH:23]=[CH:22][NH:21][N:20]=1)([CH3:17])[CH3:16]>ClCCl>[Cl:12][C:10]1[C:9]2[C:4](=[CH:5][C:6]([O:13][CH3:14])=[CH:7][CH:8]=2)[N:3]=[C:2]([N:21]2[CH:22]=[CH:23][C:19]([NH:18][CH:15]([CH3:17])[CH3:16])=[N:20]2)[CH:11]=1

Participants

Conditions

Temperature: 115 °C

Procedure

A mixture of 2,4-dichloro-7-methoxy-quinoline (1.34 g, 5.88 mmol) and isopropyl-(1H-pyrazol-3-yl)-amine (1.10 g, 8.80 mmol) was heated at 115° C. for 3 h while stirring in a sealed tube. After ˜20 min of heating, the pressure built up in the tube was released by using a needle. The mixture was then dissolved in dichloromethane and loaded onto a silica gel column. Elution with dichloromethane and methanol afforded [1-(4-chloro-7-methoxy-quinolin-2-yl)-1H-pyrazol-3-yl]-isopropyl-amine (1.53 g, 82%).

Workup

temperatureAfter ˜20 min of heating
washElution with dichloromethane and methanol

Sources & evidence

ORD record: ord-df8c30cfdedb4966b91b1abe82198dc8
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420597B2

Reaction notes

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