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

HRID 1967744Notes

Reaction equation

HRID 1967744 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-3d6e77634caf43308ddb6195107bdf23
Source dataset
uspto-grants-2013_04
Patent number
US08420827B2

Reaction notes

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