Acetyl chloride → HCID 57595411, compound

HRID 1786037Notes

Reaction equation

HRID 1786037 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C@H:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([C:22](=[O:37])[C:23]3[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH:31]4[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]4)=[CH:25][CH:24]=3)[C@@H:14]([CH3:38])[CH2:13]2)[C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[C:48](Cl)(=[O:50])[CH3:49]>ClCCl>[C:48]([N:34]1[CH2:35][CH2:36][CH:31]([CH2:30][O:29][C:26]2[CH:27]=[CH:28][C:23]([C:22]([N:15]3[C:16]4[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=4)[C@H:12]([N:8]([C:5]4[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=4)[C:9](=[O:11])[CH3:10])[CH2:13][C@@H:14]3[CH3:38])=[O:37])=[CH:24][CH:25]=2)[CH2:32][CH2:33]1)(=[O:50])[CH3:49]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 68926408HCID 68926408, compound

Product 1

HCID 57595411HCID 57595411, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2S,4R)-N-(4-Chloro-phenyl)-N-{2-methyl-1-[4-(piperidin-4-ylmethoxy)-benzoyl]-1,2,3,4-tetrahydro-quinolin-4-yl}-acetamide (0.075 g, 0.14 mmol) was dissolved in dichloromethane at room temperature. DIEA (0.1 mL, 0.56 mmol) and acetyl chloride (0.2 mL, 2.8 mmol) was added. The reaction was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo. The crude residue was purified by silica gel chromatography (10% methanol/90% dichloromethane) to afford the product (0.049 g, 49%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe crude residue was purified by silica gel chromatography (10% methanol/90% dichloromethane)

Sources & evidence

ORD record
ord-fa551e689318482c890d0cab8c473395
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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