Acetyl chloride → HCID 118075781, compound

HRID 1051734Notes

Reaction equation

HRID 1051734 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH3:5][C@H:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[C:12]=2[O:16][CH2:17][CH2:18][CH3:19])[N:7]1[C:26](=[O:28])[CH3:27].C(N(CC)CC)C>ClCCl>[C:26]([N:7]1[C:8]2[C:13](=[C:12]([O:16][CH2:17][CH2:18][CH3:19])[C:11]([CH:20]3[CH2:25][CH2:24][N:23]([C:1](=[O:3])[CH3:2])[CH2:22][CH2:21]3)=[CH:10][CH:9]=2)[CH2:14][CH2:15][C@@H:6]1[CH3:5])(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 118076148HCID 118076148, compound

Product 1

HCID 118075781HCID 118075781, compoundYield 72.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (6 μL, 0.08 mmol) was added to a solution of (S)-1-(2-methyl-6-(piperidin-4-yl)-5-propoxy-3,4-dihydroquinolin-1(2H)-yl)ethanone (26.1 mg, 0.07 mmol) and triethylamine (0.03 mL, 0.21 mmol) in dichloromethane (1.0 mL), and the reaction stirred at room temperature overnight. The reaction solution was purified directly via column chromatography on silica gel (Biotage 10 g column, gradient elution with 10-20% methanol in ethyl acetate) to afford (S)-1-(4-(1-acetyl-2-methyl-5-propoxy-1,2,3,4-tetrahydroquinolin-6-yl)piperidin-1-yl)ethan-1-one (19 mg, 71%) as an off-white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.98-1.05 (m, 6H), 1.17-1.29 (m, 1H), 1.38-1.47 (m, 1H), 1.54-1.59 (m, 1H), 1.65-1.81 (m, 5H), 2.01 (s, 6H), 2.16-2.35 (m, 2H), 2.48-2.59 (m, 1H), 2.71-2.78 (m, 1H), 3.01-3.03 (m, 2H), 3.55-3.76 (m, 2H), 3.90 (br d, J=14.66 Hz, 1H), 4.52 (br d, J=13.20 Hz, 1H), 7.04 (br s, 2H). MS (ESI, pos. ion) m/z 373 [M+H]+.

Workup

  1. customThe reaction solution was purified directly via column chromatography on silica gel (Biotage 10 g column, gradient elution with 10-20% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-3243d017cd8e4f689f57c34c9805b486
Source dataset
uspto-grants-2016_07
Patent number
US09388161B2

Reaction notes

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