Triethylamine → (rac)-N-(4-(1-Methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-5,6,7,8-tetrahydroisoquinolin-8-yl)ethanesulfonamide

HRID 530348Notes

Reaction equation

HRID 530348 reaction equation
[NH2:1][CH:2]1[C:11]2[CH:10]=[N:9][CH:8]=[C:7]([C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]([CH3:22])[C:17](=[O:23])[CH2:16][CH2:15]4)[C:6]=2[CH2:5][CH2:4][CH2:3]1.[CH2:24]([S:26](Cl)(=[O:28])=[O:27])[CH3:25].CCN(CC)CC>C(Cl)Cl>[CH3:22][N:18]1[C:19]2[C:14](=[CH:13][C:12]([C:7]3[C:6]4[CH2:5][CH2:4][CH2:3][CH:2]([NH:1][S:26]([CH2:24][CH3:25])(=[O:28])=[O:27])[C:11]=4[CH:10]=[N:9][CH:8]=3)=[CH:21][CH:20]=2)[CH2:15][CH2:16][C:17]1=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 71538469Baxdrostat Impurity 30

Product 1

HCID 71536222(rac)-N-(4-(1-Methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-5,6,7,8-tetrahydroisoquinolin-8-yl)ethanesulfonamideYield 125.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A cooled (0° C.) brown solution of (rac)-6-(8-amino-5,6,7,8-tetrahydroisoquinolin-4-yl)-1-methyl-3,4-dihydroquinolin-2(1H)-one (intermediate A-2) (61.5 mg, 200 μmol) in CH2Cl2 (3.0 ml) was treated with ethanesulfonyl chloride (65.6 mg, 48.3 μL, 500 μmol) and Et3N (40.5 mg, 55.8 μL, 400 μmol). After ½ h the mixture was concentrated in vacuo and purified by flash chromatography (20 g SiO2, Telos-cartridge, CH2Cl2/MeOH (1 to 5%)) to give 100 mg of the title compound together with Et3N×HCl as impurity. Extraction with H2O/EtOAc (3×), and precipitation CH2Cl2/n-pentane gave the pure title compound (46 mg, 58%) as a yellow powder. MS: 400.2 (M+H+).

Workup

  1. concentrationAfter ½ h the mixture was concentrated in vacuo
  2. custompurified by flash chromatography (20 g SiO2, Telos-cartridge, CH2Cl2/MeOH (1 to 5%))

Sources & evidence

ORD record
ord-bd8751af0e7545e78305338878a5ec58
Source dataset
uspto-grants-2016_05
Patent number
US09353081B2

Reaction notes

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