Acetyl chloride → HCID 21092882, compound

HRID 1785935Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C@H:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]([C:19]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)=[O:20])[C@@H:11]([CH3:28])[CH2:10]2)=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[C:38](Cl)(=[O:40])[CH3:39]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]([C:19](=[O:20])[C:21]3[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=3)[CH:11]([CH3:28])[CH2:10]2)[C:38](=[O:40])[CH3:39])=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 6367Acetyl chloride

HCID 81531Diisopropylethylamine

HCID 58859890HCID 58859890, compound

Product 1

HCID 21092882HCID 21092882, compoundYield 71%

Procedure

To a solution of (2S,4R)-[4-(4-chloro-phenylamino)-2-methyl-3,4-dihydro-2H-quinolin-1-yl]-(4-fluoro-phenyl)-methanone (250 mg, 0.636 mmol) in acetyl chloride (5 mL) was added diisopropylethylamine (120 uL, 0.70 mmol). The mixture was stirred at rt 4 h. The mixture was concentrated under reduced pressure, dissolved in ethyl acetate, washed with sat. aqueous sodium bicarbonate, brine and dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (25/75 hexanes/ethyl acetate gradient) to afford pure N-(4-chloro-phenyl)-N-[1-(4-fluoro-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide (200 mg, 71%).

Workup

concentrationThe mixture was concentrated under reduced pressure
dissolutiondissolved in ethyl acetate
washwashed with sat. aqueous sodium bicarbonate, brine
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel chromatography (25/75 hexanes/ethyl acetate gradient)

Sources & evidence

ORD record: ord-7d5cd33344af40e2a4eb5b7e6e8f6f65
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07504508B2

Reaction notes

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