Diisopropylethylamine → 2-(3,5-Bis-trifluoromethyl-phenyl)-N-[4-iodo-6-(4-methyl-piperazin-1-yl)-pyridin-3-yl]-isobutyramide

HRID 1348558Notes

Reaction equation

HRID 1348558 reaction equation
[I:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)[N:5]=[CH:4][C:3]=1[NH2:15].C(N(CC)C(C)C)(C)C.[F:25][C:26]([F:44])([F:43])[C:27]1[CH:28]=[C:29]([C:37]([CH3:42])([CH3:41])[C:38](Cl)=[O:39])[CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:32]=1>ClCCl>[F:25][C:26]([F:43])([F:44])[C:27]1[CH:28]=[C:29]([C:37]([CH3:41])([CH3:42])[C:38]([NH:15][C:3]2[CH:4]=[N:5][C:6]([N:8]3[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]3)=[CH:7][C:2]=2[I:1])=[O:39])[CH:30]=[C:31]([C:33]([F:34])([F:35])[F:36])[CH:32]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 112671412-(3,5-Bis(trifluoromethyl)phenyl)-2-methylpropanoyl chlorideHCID 210916424-Iodo-6-(4-methyl-piperazin-1-yl)-pyridin-3-ylamine

Product 1

HCID 210916402-(3,5-Bis-trifluoromethyl-phenyl)-N-[4-iodo-6-(4-methyl-piperazin-1-yl)-pyridin-3-yl]-isobutyramideYield 112.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 1.60 g (5.03 mmol) 4-iodo-6-(4-methyl-piperazin-1-yl)-pyridin-3-ylamine and 975 mg (7.54 mmol) N,N-diisopropyl ethyl amine in 16 ml dichloromethane was added dropwise 1.76 g (5.53 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-2-methyl-propionyl chloride at 0° C. The reaction mixture was stirred for 2 h at room temperature and 2 h at reflux. After cooling to room temperature the reaction mixture was washed with 20 ml of a 1 M aqueous sodium carbonate solution and 20 ml water. The combined organic layers were dried over sodium sulfate and concentrated in vacuo to give 3.39 g (100%) of the crude title compound as a brown oil.

Workup

  1. temperatureat reflux
  2. temperatureAfter cooling to room temperature the reaction mixture
  3. washwas washed with 20 ml of a 1 M aqueous sodium carbonate solution and 20 ml water
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d113e0255ddd4a95b781dda3acb68082
Source dataset
uspto-grants-2007_05
Patent number
US07211579B2

Reaction notes

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