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

HRID 540144Notes

Reaction equation

HRID 540144 reaction equation
[CH3:1][CH:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[S:6][CH2:5][CH2:4][NH:3]1.Cl[C:14]1[CH:23]=[C:22]([Cl:24])[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([CH3:25])[CH:20]=2)[N:15]=1>>[Cl:24][C:22]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([CH3:25])[CH:20]=2)[N:15]=[C:14]([N:3]2[CH:2]([CH3:1])[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[S:6][CH2:5][CH2:4]2)[CH:23]=1

Participants

3

Reactant 2

HCID 27546682,4-Dichloro-6-methylquinolineHCID 866913675-Methyl-2,3,4,5-tetrahydro-1,4-benzothiazepine

Product 1

HCID 712544444-(4-Chloro-6-methylquinolin-2-yl)-5-methyl-2,3,4,5-tetrahydro-1,4-benzothiazepineYield 28.3%

Conditions

Temperature
170 °C

Procedure

A mixture of 5-methyl-2,3,4,5-tetrahydro-1,4-benzothiazepine (1.0 g, 5.58 mmol) and 2,4-dichloro-6-methylquinoline (1.7 g, 8.02 mmol) was heated with stirring in a 2 mL of microwave process vial for 5 hours at 170° C. under microwave irradiation. The solvent was removed by concentration in vacuo. The residue was purified by flash column chromatography to give 560 mg of the mixture of 5-methyl-2,3,4,5-tetrahydro-1,4-benzothiazepine and 4-(4-chloro-6-methylquinolin-2-yl)-5-methyl-2,3,4,5-tetrahydro-1,4-benzothiazepine.

Workup

  1. temperaturewas heated
  2. customThe solvent was removed by concentration in vacuo
  3. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-946e1e009c0243be913f8e44e5a2086a
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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