Tetrahydro-1,4-benzodiazepin-2-one → 4-(4-Chloro-6-methylquinolin-2-yl)-1,3,4,5-tetrahydro-2H-1,4-benzodiazepin-2-one

HRID 540345Notes

Reaction equation

Cl[C:2]1[CH:11]=[C:10]([Cl:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:13])[CH:8]=2)[N:3]=1.[NH:14]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH2:18][NH:17][CH2:16][C:15]1=[O:25]>C(O)CCC>[Cl:12][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:13])[CH:8]=2)[N:3]=[C:2]([N:17]2[CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[NH:14][C:15](=[O:25])[CH2:16]2)[CH:11]=1

Participants

Conditions

Temperature: 160 °C

Procedure

The mixture of 2,4-dichloro-6-methyl-quinoline (422 mg, 2 mmol), 1,3,4,5-tetrahydro-2H-1,4-benzodiazepin-2-one (298 mg, 2 mmol) and n-butyl alcohol (15 mL) was heated with stirring in a 20 mL microwave process vial for 3 hours at 160° C. under microwave irradiation. After cooling, the solvent was removed in vacuo and the residue was purified by column chromatography on silica gel (methanol/dichloromethane, 1:20) to give the product. MS obsd. (ESI+) [(M+H)+] 338.

Workup

temperaturewas heated
temperatureAfter cooling
customthe solvent was removed in vacuo
customthe residue was purified by column chromatography on silica gel (methanol/dichloromethane, 1:20)
customto give the product

Sources & evidence

ORD record: ord-f88a7fd5d48a4b2ab4c949aa725c35c5
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871756B2

Reaction notes

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