Potassium Carbonate → ethyl-2-[4-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-1-piperazinyl]-4-thiazolecarboxylate

HRID 2043781Notes

Reaction equation

HRID 2043781 reaction equation
C(OC(C1N=C(C2[CH2:16][CH2:15][N:14]([C:17](=[O:29])[CH2:18][N:19]3[C:23]([CH3:24])=[CH:22][C:21]([C:25]([F:28])([F:27])[F:26])=[N:20]3)[CH2:13][CH2:12]2)SC=1)=O)C.Cl.N1(C2SC=C(C(O)=O)N=2)CCNCC1.Cl.[N:46]1([C:52]2[S:53][CH:54]=[C:55]([C:57]([O:59][CH2:60][CH3:61])=[O:58])[N:56]=2)CCNCC1.C(=O)([O-])[O-].[K+].[K+]>ClCCl.C(N(CC)CC)C>[CH2:60]([O:59][C:57]([C:55]1[N:56]=[C:52]([N:46]2[CH2:12][CH2:13][N:14]([C:17](=[O:29])[CH2:18][N:19]3[C:23]([CH3:24])=[CH:22][C:21]([C:25]([F:26])([F:27])[F:28])=[N:20]3)[CH2:15][CH2:16]2)[S:53][CH:54]=1)=[O:58])[CH3:61]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 66911511ethyl-2-[1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-4-thiazolecarboxylateHCID 674628182-(1-Piperazinyl)-4-thiazolecarboxylate monohydrochlorideHCID 67463024Ethyl 2-(1-piperazinyl)-4-thiazolecarboxylate monohydrochloride

Product 1

HCID 67460845ethyl-2-[4-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-1-piperazinyl]-4-thiazolecarboxylate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 8471TriethylamineSolvent

Procedure

5-Methyl-3-(trifluoromethyl)-1H-pyrazole-1-acetyl chloride (1.05 g, 2.5 mmol) (prepared as described in Example 19, step B) was dissolved in 10 mL of dichloromethane and added to a mixture of 2-(1-piperazinyl)-4-thiazolecarboxylate monohydrochloride (1.0 g, 3.0 mmol) (i.e. the product of Example 30, Step B) and powdered anhydrous potassium carbonate (2.2 g, 15.9 mmol) in 20 mL of dichloromethane at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for 3 h. Then triethylamine (2 mL) was added to the reaction mixture, and the stirring was continued for an additional 30 minutes. The reaction mixture was diluted with dichloromethane, washed with 1 N aqueous hydrochloric acid, water, saturated aqueous solution of sodium bicarbonate and brine, and dried over magnesium sulfate. The filtered residue was evaporated in vacuo to give 1.0 g of a white foam. The resulting foam was slurried in 1-chlorobutane and filtered to give 0.83 g of the title compound as a white solid.

Workup

  1. customat 0° C
  2. waitthe stirring was continued for an additional 30 minutes
  3. washwashed with 1 N aqueous hydrochloric acid, water, saturated aqueous solution of sodium bicarbonate and brine
  4. dry with materialdried over magnesium sulfate
  5. customThe filtered residue was evaporated in vacuo

Sources & evidence

ORD record
ord-db18e7ef5fd348579084ea4d4e5c8839
Source dataset
uspto-grants-2013_11
Patent number
US08586611B2

Reaction notes

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