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

HRID 1361767Notes

Reaction equation

HRID 1361767 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]

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-c916516bcec24f1888750b3aad52f92c
Source dataset
uspto-grants-2011_02
Patent number
US07880013B2

Reaction notes

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