2,4-Dichloro-6-methylquinoline → 4-(4-Chloro-6-methylquinolin-2-yl)-8-methoxy-2,3,4,5-tetrahydro-1,4-benzothiazepine

HRID 539993Notes

Reaction equation

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

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of 8-methoxy-2,3,4,5-tetrahydro-1,4-benzothiazepine (0.63 g, 3.2 mmol), 2,4-dichloro-6-methylquinoline (0.68 g, 3.2 mmol) and n-butanol (4 mL) was heated with stirring in a 5 mL of microwave process vial for 2.5 hours at 160° C. under microwave irradiation. The solvent was removed by concentration in vacuo. The residue was dissolved in a mixture solvent of ethanol and dichloromethane and then concentrated in vacuo to remove dichloromethane. The formed precipitate was collected by filtration, which was washed with diethyl ether and petroleum ether, dried in vacuo to afford 0.59 g of the product as a pale white solid (yield was 50%). MS obsd. (ESI+) [(M+H)+] 371.

Workup

temperaturewas heated
customThe solvent was removed by concentration in vacuo
dissolutionThe residue was dissolved in a mixture solvent of ethanol and dichloromethane
concentrationconcentrated in vacuo
customto remove dichloromethane
filtrationThe formed precipitate was collected by filtration, which
washwas washed with diethyl ether and petroleum ether
customdried in vacuo

Sources & evidence

ORD record: ord-4e1218206b1b4e1eba2589a356cb2bdd
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871756B2

Reaction notes

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