Methyl iodide → Methyl 1-(5-(3-fluorophenyl)-2-methylthiazole-4-carbonyl)-5-methoxypiperidine-2-carboxylate

HRID 60826Notes

Reaction equation

HRID 60826 reaction equation
[CH3:1]I.[F:3][C:4]1[CH:5]=[C:6]([C:10]2[S:14][C:13]([CH3:15])=[N:12][C:11]=2[C:16]([N:18]2[CH2:23][CH:22]([OH:24])[CH2:21][CH2:20][CH:19]2[C:25]([O:27][CH3:28])=[O:26])=[O:17])[CH:7]=[CH:8][CH:9]=1>CC#N.C(Cl)Cl>[F:3][C:4]1[CH:5]=[C:6]([C:10]2[S:14][C:13]([CH3:15])=[N:12][C:11]=2[C:16]([N:18]2[CH2:23][CH:22]([O:24][CH3:1])[CH2:21][CH2:20][CH:19]2[C:25]([O:27][CH3:28])=[O:26])=[O:17])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 89739369HCID 89739369, compound

Product 1

HCID 89739844Methyl 1-(5-(3-fluorophenyl)-2-methylthiazole-4-carbonyl)-5-methoxypiperidine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

MeI (6.8 mmol, 0.43 mL) was added to a mixture of methyl 1-(5-(3-fluorophenyl)-2-methylthiazole-4-carbonyl)-5-hydroxypiperidine-2-carboxylate (0.68 mmol, 0.26 g) and Ag2O (3.4 mmol, 0.8 g) in CH3CN (3 mL) at rt. The resulting mixture was stirred at rt for two days. The reaction mixture was diluted with DCM and filtered through a pad of diatomaceous earth. The filtrate was concentrated in vacuo to give desired product methyl 1-(5-(3-fluorophenyl)-2-methylthiazole-4-carbonyl)-5-methoxypiperidine-2-carboxylate which was used for next step without further purification (Y: 96%).

Workup

  1. filtrationfiltered through a pad of diatomaceous earth
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-6c22ea93e8a9402bb82b99d307ff2baa
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

Loading…