Triethylamine → HCID 66868671, compound

HRID 242070

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]([O:22][CH2:23][CH2:24][NH2:25])[CH:20]=4)[C:15]([CH3:27])([CH3:26])[CH2:14][N:13]=3)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:35]([N:37]([CH2:42][CH3:43])[S:38](Cl)(=[O:40])=[O:39])[CH3:36]>ClCCl>[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]([O:22][CH2:23][CH2:24][NH:25][S:38](=[O:40])(=[O:39])[N:37]([CH2:42][CH3:43])[CH2:35][CH3:36])[CH:20]=4)[C:15]([CH3:27])([CH3:26])[CH2:14][N:13]=3)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 2.5 °C

Procedure

2-({1-[1-(4-Chlorophenyl)cyclobutyl]-4,4-dimethyl-3,4-dihydroisoquinolin-7-yl}oxy)ethanamine (145 mg, 0.38 mmol, cf. example 67) was dissolved in dry dichloromethane (8 mL). Triethylamine (60 μL, 0.45 mmol). The solution was cooled to 0-5° C. and diethylsulfamoyl chloride (71.5 mg, 0.42 mmol) was added. The reaction mixture was stirred at room temperature over night. The reaction mixture was diluted with dichloromethane (20 mL) and washed with a 1:1 mixture of water and saturated ammonium chloride solution (20 mL). The organic layer was dried (MgSO4) and the solvent was evaporated in vacuo. The crude product was purified by flash chromatography (silica, dichloromethane then dichloromethane:ethyl acetate=180:5). Yield: 96 mg (0.19 mmol, 48.9%).

Workup

washwashed with a 1:1 mixture of water and saturated ammonium chloride solution (20 mL)
dry with materialThe organic layer was dried (MgSO4)
customthe solvent was evaporated in vacuo
customThe crude product was purified by flash chromatography (silica, dichloromethane

Sources & evidence

ORD record: ord-b9a1d7aa010a4399bdbf7bd4b5e70aa1
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653100B2

Linked notes

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