Acetyl chloride → HCID 58121152, compound
Reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[S:10][C:11]=2[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:23](Cl)(=[O:25])[CH3:24]>C1COCC1.[Cl-].[Na+].O>[C:23]([N:20]1[CH2:21][CH2:22][CH:17]([C:9]2[S:10][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[N:8]=2)[CH2:18][CH2:19]1)(=[O:25])[CH3:24]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To prepare compound 90, the procedure was followed as outlined in Scheme 10, Step 2 replacing compounds 77 and 78 with compounds tent-butyl 4-carbamothioylpiperidine-1-carboxylate and ethyl 2-bromo-3-oxo-3-phenylpropanoate to afford compound 90 (0.790 g, 21% yield) as a white solid. To a stirring solution of ethyl 4-phenyl-2-(piperidin-4-yl)thiazole-5-carboxylate 90 (0.235 g, 0.743 mmol) in THF (8 mL) was added acetyl chloride (1.11 mL, 0.891 mmol) and the reaction was stirred at room temperature for 2 h. The solution was diluted with brine and extracted with ethyl acetate. The combined organics were dried over Na2SO4, filtered and concentrated under reduced pressure to afford ethyl 2-(1-acetylpiperidin-4-yl)-4-phenylthiazole-5-carboxylate 91 as a light yellow oil (0.196 g, 74% yield) after purification by flash chromatography (0 to 10% MeOH in ethyl acetate). LRMS (ESI): (calc) 358.45 (found) 359.3 (MH)+
Workup
- extractionextracted with ethyl acetate
- dry with materialThe combined organics were dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-fb0b061f68284b2fb5d1d7a7cbb85c6a
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08673911B2
Reaction notes
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