Acetyl chloride → HCID 178490768, compound

HRID 2402585Notes

Reaction equation

HRID 2402585 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][C:18]=2[S:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15](=[O:27])[N:14]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)[CH:13]=[CH:12]3)[CH2:4][CH2:3]1.C(N(CC)CC)C.[C:44](Cl)(=[O:46])[CH3:45]>ClCCl>[CH2:20]([S:19][C:18]1[CH:17]=[C:16]2[C:11]([CH:12]=[CH:13][N:14]([CH2:28][C:29]3[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=3)[C:15]2=[O:27])=[CH:10][C:9]=1[O:8][C@@H:5]1[CH2:4][CH2:3][C@H:2]([NH:1][C:44](=[O:46])[CH3:45])[CH2:7][CH2:6]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 178490767HCID 178490767, compound

Product 1

HCID 178490768HCID 178490768, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

45 mg (0.073 mmol) of 6-(4-amino-cis-cyclohexyloxy)-7-benzylsulfanyl-2-(4-methoxybenzyl)-2H-iso-quinolin-1-one (127) were dissolved in 5 ml of dichloromethane and 14.8 mg (0.146 mmol) of triethylamine were added. At 0° C., 6.9 mg (0.088 mmol) of acetylchloride were added and the solution was stirred at room temperature. After 2 h, dichloromethane was added and the solution was washed with 2 N HCl and saturated sodium bicarbonate solution. After drying with magnesium sulfate and evaporation of the solvent, the title compound was isolated as crude product, which was used without further purification. Rt=1.53 min (Method C). Detected mass: 543.6 (M+H+).

Workup

  1. washthe solution was washed with 2 N HCl and saturated sodium bicarbonate solution
  2. dry with materialAfter drying with magnesium sulfate and evaporation of the solvent

Sources & evidence

ORD record
ord-b72ebdbb6417499bb23202be01b499d1
Source dataset
uspto-grants-2014_08
Patent number
US08796458B2

Reaction notes

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