Diisopropylethylamine → 6-[4-(5-Fluoro-2-trifluoromethylbenzoyl)piperazin-1-YL]imidazo[1,2-B]pyridazine-2-carboxylic acid ethyl ester

HRID 1985633Notes

Reaction equation

HRID 1985633 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)=[N:10][N:9]2[CH:20]=1)=[O:5])[CH3:2].C(N(C(C)C)CC)(C)C.[F:30][C:31]1[CH:32]=[CH:33][C:34]([C:40]([F:43])([F:42])[F:41])=[C:35]([CH:39]=1)[C:36](Cl)=[O:37]>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:19][CH2:18][N:17]([C:36](=[O:37])[C:35]4[CH:39]=[C:31]([F:30])[CH:32]=[CH:33][C:34]=4[C:40]([F:43])([F:41])[F:42])[CH2:16][CH2:15]3)=[N:10][N:9]2[CH:20]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27375605-Fluoro-2-(trifluoromethyl)benzoyl chlorideHCID 668640036-Piperazin-1-ylimidazo[1,2-b]pyridazine-2-carboxylic acid ethyl ester

Product 1

HCID 668634596-[4-(5-Fluoro-2-trifluoromethylbenzoyl)piperazin-1-YL]imidazo[1,2-B]pyridazine-2-carboxylic acid ethyl esterYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 6-piperazin-1-ylimidazo[1,2-b]pyridazine-2-carboxylic acid ethyl ester (1.016 g, 3.69 mmol) and diisopropylethylamine (1.29 mL, 7.38 mmol) in anhydrous dichloromethane (20 mL) was added 5-fluoro-2-trifluoromethylbenzoyl chloride dropwise at room temperature. The reaction mixture was stirred at room temperature for 15 minutes, then diluted with dichloromethane and washed with water. The organic layer was dried and concentrated in vacuo. The title compound was obtained in 82% yield (1.365 g) after purification by column chromatography.

Workup

  1. washwashed with water
  2. customThe organic layer was dried
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b6abe68b91a44bf38cb5c4c2c28d91ae
Source dataset
uspto-grants-2009_06
Patent number
US07547698B2

Reaction notes

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