Ammonia → N-[4-(2-Furyl)-5-morpholinothiazol-2-yl]piperidine-4-carboxamide

HRID 337415

Reaction equation

HRID 337415 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([C:17]([NH:19][C:20]2[S:21][C:22]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)=[C:23]([C:25]3[O:26][CH:27]=[CH:28][CH:29]=3)[N:24]=2)=[O:18])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.CSC.N>ClCCl>[O:26]1[CH:27]=[CH:28][CH:29]=[C:25]1[C:23]1[N:24]=[C:20]([NH:19][C:17]([CH:14]2[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]2)=[O:18])[S:21][C:22]=1[N:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 1068Dimethyl SulfideHCID 231441071-(Benzyloxycarbonyl)-N-[4-(2-furyl)-5-morpholinothiazol-2-yl]piperidine-4-carboxamide

Product 1

HCID 23144542N-[4-(2-Furyl)-5-morpholinothiazol-2-yl]piperidine-4-carboxamideYield 39.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 43 (4.71 g, 9.50 mmol) was dissolved in dichloromethane (100 mL), and dimethyl sulfide (29.4 mL, 400 mmol) and boron trifluoride-diethyl ether complex (24.6 mL, 200 mmol) were added thereto, followed by stirring overnight at room temperature. The reaction mixture was poured into 28% aqueous ammonia, followed by extraction with chloroform. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure to afford the entitled Compound 44 (1.36 g, 38%).

Workup

  1. extractionfollowed by extraction with chloroform
  2. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-f9b9fd75b1604554b8965446ac5f9580
Source dataset
uspto-grants-2014_11
Patent number
US08889718B2

Linked notes

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