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Acetic Anhydride → 1-Acetyl-N-[4-(2-furyl)-5-morpholinothiazol-2-yl]piperidine-4-carboxamide

HRID 2238711
Notes
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Reaction equation

HRID 2238711 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:7]=[C:8]([NH:17][C:18]([CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[O:19])[S:9][C:10]=1[N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.[C:26](OC(=O)C)(=[O:28])[CH3:27]>N1C=CC=CC=1>[C:26]([N:23]1[CH2:24][CH2:25][CH:20]([C:18]([NH:17][C:8]2[S:9][C:10]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[C:6]([C:2]3[O:1][CH:5]=[CH:4][CH:3]=3)[N:7]=2)=[O:19])[CH2:21][CH2:22]1)(=[O:28])[CH3:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 23144542N-[4-(2-Furyl)-5-morpholinothiazol-2-yl]piperidine-4-carboxamide

Product 1

HCID 231444871-Acetyl-N-[4-(2-furyl)-5-morpholinothiazol-2-yl]piperidine-4-carboxamideYield 25%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Compound 44 (145 mg, 0.400 mmol) was dissolved in pyridine (5 mL), acetic anhydride (0.19 mL, 2.00 mmol) was added thereto, followed by stirring at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified through silica gel column chromatography (ethyl acetate:methanol=9:1) to afford the entitled Compound 54 (40.0 mg, 25%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe resulting residue was purified through silica gel column chromatography (ethyl acetate:methanol=9:1)

Sources & evidence

ORD record
ord-7b93b5c6197e43abaa4f003688e41341
Source dataset
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07718808B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes