HCID 58246337, compound → HCID 58246390, compound

HRID 242049Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([NH2:22])[CH:20]=4)[CH2:15][CH2:14][N:13]=3)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1>Br.C(O)(=O)C.[OH-].[Na+]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:12]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([N:22]5[CH2:15][CH2:14][NH:13][CH2:12][CH2:8]5)[CH:20]=4)[CH2:15][CH2:14][N:13]=3)[CH2:11][CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

1-[1-(4-Chloro-phenyl)-cyclobutyl]-3,4-dihydro-isoquinolin-7-ylamine (400 mg, 0.75 mmol) was dissolved in HBr/acetic acid (10 ml, 33%) and stirred for 3 h at 70° C. Another 10 ml of the HBr/acetic acid solution was added and the mixture was stirred for another 8 h at 70° C. The solvent was diluted with 1 N sodium hydroxid solution and extracted with dichloromethane. The combined organic layers were washed with saturated sodium chloride solution and dried with sodium sulphate. The residue was purified by flash column chromatography on silica with dichloromethane/methanol 98:2->95:5. The product was obtained as a brown oil (100 mg, 0.26 mmol, 35%) that was sufficiently pure for the next step.

Workup

stirringthe mixture was stirred for another 8 h at 70° C
extractionextracted with dichloromethane
washThe combined organic layers were washed with saturated sodium chloride solution
dry with materialdried with sodium sulphate
customThe residue was purified by flash column chromatography on silica with dichloromethane/methanol 98:2->95:5

Sources & evidence

ORD record: ord-56637800766548b09c41331180304e31
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653100B2

Reaction notes

Loading…