Sodium Iodide → Methyl 2-{4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl}-1,3-thiazole-5-carboxylate

HRID 2074147Notes

Reaction equation

HRID 2074147 reaction equation
COC([C:5]1([NH2:10])[NH:9][CH:8]=[CH:7][S:6]1)=O.Cl[CH2:12][CH2:13][N:14]([CH2:27][CH2:28]Cl)[C:15](=[O:26])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]([F:25])([F:24])[F:23].[C:30]([O-:33])([O-])=[O:31].[K+].[K+].[Na+].[I-].[CH3:38]OCCOC>>[CH3:38][O:33][C:30]([C:7]1[S:6][C:5]([N:10]2[CH2:28][CH2:27][N:14]([C:15](=[O:26])[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]([F:25])([F:24])[F:23])[CH2:13][CH2:12]2)=[N:9][CH:8]=1)=[O:31]

Participants

6

Reactant 5

HCID 5238Sodium IodideHCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 66584130HCID 66584130, compoundHCID 66584328HCID 66584328, compound

Product 1

HCID 57659020Methyl 2-{4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl}-1,3-thiazole-5-carboxylate

Procedure

A reaction mixture of 2-aminothiazole-2-carboxylic acid methyl ester (0.790 g, 5.0 mmol), N,N-bis(2-chloroethyl)-2-trifluoromethylbenzamide (1.880 g, 6 mmol), K2CO3 (1.0 g, 7.2 mmol), and NaI (0.2 g) in 1,2-dimethoxyethane (20 mL) was heated to reflux for 24 hours. The solvent was removed by evaporation, and the residue was dissolved in ethyl acetate, washed with water and brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by column chromatography to give 2-[4-(2-trifluoromethylbenzoyl)piperazin-1-yl]thiazole-5-carboxylic acid methyl ester (0.317 g) which was used for next step without further purification.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 24 hours
  3. customThe solvent was removed by evaporation
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washwashed with water and brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-e5bd44c58aa342668746aa92728865bf
Source dataset
uspto-grants-2011_04
Patent number
US07919496B2

Reaction notes

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