2-Dimethylaminopyridine → HCID 59295414, compound

HRID 2233305Notes

Reaction equation

HRID 2233305 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[S:16][C:15]([CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[N:14][C:13]=2[CH3:23])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(N(CC)C(C)C)(C)C.CN(C1C=CC=CN=1)C.[F:42][C:43]([F:49])([F:48])[S:44](Cl)(=[O:46])=[O:45]>ClCCl>[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[S:16][C:15]([CH:17]3[CH2:22][CH2:21][N:20]([S:44]([C:43]([F:49])([F:48])[F:42])(=[O:46])=[O:45])[CH2:19][CH2:18]3)=[N:14][C:13]=2[CH3:23])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

6

Reactant 4

HCID 218852-DimethylaminopyridineHCID 79000Trifluoromethanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 59295393HCID 59295393, compound

Product 1

HCID 59295414HCID 59295414, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

500 mg 2-Chloro-4-(4-methyl-2-piperidin-4-yl-thiazol-5-ylmethoxy)-benzonitrile was dissolved in 20 ml dichloromethane. 0.25 ml N,N-Diisopropylethylamine and 50 mg dimethylaminopyridine were added. Then 0.26 ml trifluoromethanesulfonylchloride were added to the ice cooled reaction mixture. The cooling bath was removed and the reaction mixture stirred at room temperature overnight. The reaction mixture was washed with 10 ml saturated NaHCO3 solution and then dried over MgSO4. The solvent was removed in Vacuo. The resulting crude material was purified by reversed phase HPLC to obtain 350 mg 2-Chloro-4-[4-methyl-2-(1-trifluoromethanesulfonyl-piperidin-4-yl)-thiazol-5-ylmethoxy]-benzonitrile as amorphous solid.

Workup

  1. temperaturecooled
  2. customreaction mixture
  3. customThe cooling bath was removed
  4. washThe reaction mixture was washed with 10 ml saturated NaHCO3 solution
  5. dry with materialdried over MgSO4
  6. customThe solvent was removed in Vacuo
  7. customThe resulting crude material was purified by reversed phase HPLC

Sources & evidence

ORD record
ord-53ee299b1a134e8585a7c1f4619f998e
Source dataset
uspto-grants-2010_05
Patent number
US07709481B2

Reaction notes

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