Pyridine → HCID 57986899, compound

HRID 871924Notes

Reaction equation

HRID 871924 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([F:21])([C:14]2[S:15][C:16]([CH2:19]O)=[CH:17][N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.CS([Cl:32])(=O)=O>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:14]2[S:15][C:16]([CH2:19][Cl:32])=[CH:17][N:18]=2)([F:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 57986840HCID 57986840, compound

Product 1

HCID 57986899HCID 57986899, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-fluoro-4-(5-hydroxymethyl-thiazol-2-yl)-piperidine-1-carboxylic acid tert-butyl ester (1.34 g, 4.24 mmol) and pyridine (426 mg, 1.3 eq.) in CH2Cl2 (30 mL) at 0° C. was added MsCl (631 mg, 1.3 eq.). The mixture was warmed to room temperature and stirred overnight. The reaction mixture was washed with saturated NaHCO3 solution and dried over Na2SO4. Removal of the solvent afforded the desired product, which was used directly in the following reaction without further purification.

Workup

  1. washThe reaction mixture was washed with saturated NaHCO3 solution
  2. dry with materialdried over Na2SO4
  3. customRemoval of the solvent

Sources & evidence

ORD record
ord-fdb7dbad5c114b33bd56ada0e02725e1
Source dataset
uspto-grants-2015_03
Patent number
US08975258B2

Reaction notes

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