Trifluoroacetic acid → HCID 59295393, compound

HRID 2233304Notes

Reaction equation

HRID 2233304 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[S:15][C:16]([CH2:20][O:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[C:24]([Cl:30])[CH:23]=3)=[C:17]([CH3:19])[N:18]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(OC(N1CCC(C2SC(CCl)=C(C)N=2)CC1)=O)(C)(C)C.ClC1C=C(O)C=CC=1C#N.FC(F)(F)C(O)=O>ClCCl>[Cl:30][C:24]1[CH:23]=[C:22]([O:21][CH2:20][C:16]2[S:15][C:14]([CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[N:18][C:17]=2[CH3:19])[CH:27]=[CH:26][C:25]=1[C:28]#[N:29]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 5927972-Chloro-4-hydroxybenzonitrileHCID 59295386HCID 59295386, compoundHCID 59295436HCID 59295436, compound

Product 1

HCID 59295393HCID 59295393, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.5 g 4-[5-(3-Chloro-4-cyano-phenoxymethyl)-4-methyl-thiazol-2-yl]-piperidine-1-carboxylic acid tert-butyl ester (derived from 4-(5-Chloromethyl-4-methyl-thiazol-2-yl)-piperidine-1-carboxylic acid tert-butyl ester and commercially available 2-Chloro-4-hydroxy-benzonitrile according to the method described in Example 1) was dissolved in 100 ml dichloromethane. 20 ml trifluoroacetic acid were added and the reaction mixture stirred at room temperature for one hour. The solvent was removed in vacuo and the residue was dissolved in 200 ml ethyl acetate, washed three times with saturated NaHCO3 solution and then dried over MgSO4. The solvent was removed in Vacuo to obtain 3.5 g 2-Chloro-4-(4-methyl-2-piperidin-4-yl-thiazol-5-ylmethoxy)-benzonitrile as colorless solid.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in 200 ml ethyl acetate
  3. washwashed three times with saturated NaHCO3 solution
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed in Vacuo

Sources & evidence

ORD record
ord-1ea92bcff98f40d0b59cc1ded35fedf6
Source dataset
uspto-grants-2010_05
Patent number
US07709481B2

Reaction notes

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