Triethylamine → N-[4-(1-(2-Pyrimidyl)-4-piperazinyl)-2-butynyl]-1,2-benzisothiazole-3-carboxamide

HRID 483437Notes

Reaction equation

HRID 483437 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C:10](Cl)=[O:11])=[N:2]1.[N:13]1[CH:18]=[CH:17][CH:16]=[N:15][C:14]=1[N:19]1[CH2:24][CH2:23][N:22]([CH2:25][C:26]#[C:27][CH2:28][NH2:29])[CH2:21][CH2:20]1.C(N(CC)CC)C>ClCCl.O>[N:13]1[CH:18]=[CH:17][CH:16]=[N:15][C:14]=1[N:19]1[CH2:24][CH2:23][N:22]([CH2:25][C:26]#[C:27][CH2:28][NH:29][C:10]([C:3]2[C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[S:1][N:2]=2)=[O:11])[CH2:21][CH2:20]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 15639471Benzo[d]isothiazole-3-carbonyl chlorideHCID 197523271-(2-Pyrimidyl)-4-(4-amino-2-butynyl)piperazine

Product 1

HCID 19752316N-[4-(1-(2-Pyrimidyl)-4-piperazinyl)-2-butynyl]-1,2-benzisothiazole-3-carboxamideYield 72.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1,2-benzisothiazole-3-carboxylic acid chloride (2.55 g) and 1-(2-pyrimidyl)-4-(4-amino-2-butynyl)piperazine (3.0 g) in dichloromethane (100 ml) was stirred while triethylamine (3.62 ml) was added dropwise. Stirring was continued overnight. After 24 hr, the reaction mixture was diluted with water, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated in vacuo. The resiude was recrystallized from dichloromethane/ether/hexane to provide 3.67 g (72.3%) of product, mp 102°-104° C.

Workup

  1. additionwas added dropwise
  2. waitAfter 24 hr
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe resiude was recrystallized from dichloromethane/ether/hexane

Sources & evidence

ORD record
ord-fcfab8f288e24b9684d1bfced7a069e3
Source dataset
uspto-grants-1993_07
Patent number
US05225412

Reaction notes

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