Water → 2-(3-(4-(2-pyrimidinyl)-1-piperazinyl)propyl)-7-methoxy-1,2,4-benzothiadiazin-3(4H)one 1,1dioxide

HRID 2108169Notes

Reaction equation

HRID 2108169 reaction equation
Br[CH2:2][CH2:3][CH2:4][N:5]1[C:10](=[O:11])[NH:9][C:8]2[CH:12]=[CH:13][C:14]([O:16][CH3:17])=[CH:15][C:7]=2[S:6]1(=[O:19])=[O:18].[N:20]1[CH:25]=[CH:24][CH:23]=[N:22][C:21]=1[N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.C(N(CC)CC)C.O>CN(C=O)C>[N:20]1[CH:25]=[CH:24][CH:23]=[N:22][C:21]=1[N:26]1[CH2:31][CH2:30][N:29]([CH2:2][CH2:3][CH2:4][N:5]2[C:10](=[O:11])[NH:9][C:8]3[CH:12]=[CH:13][C:14]([O:16][CH3:17])=[CH:15][C:7]=3[S:6]2(=[O:19])=[O:18])[CH2:28][CH2:27]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 887471-(2-Pyrimidinyl)piperazineHCID 190234312-(3-bromopropyl)-7-methoxy-1,2,4-benzothiadiazin-3(4H)one 1,1-dioxide

Product 1

HCID 190234012-(3-(4-(2-pyrimidinyl)-1-piperazinyl)propyl)-7-methoxy-1,2,4-benzothiadiazin-3(4H)one 1,1dioxide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

0.01 mol of 2-(3-bromopropyl)-7-methoxy-1,2,4-benzothiadiazin-3(4H)one 1,1-dioxide, 0.012 mol of 1-(2-pyrimidinyl)piperazine and 0.01 mol of triethylamine are dissolved in 30 ml of DMF and the solution is heated at 60° C., with stirring, for 1.5 hours. Then 15 ml of water are added and the reaction mixture is cooled to 0° C. The substance which crystallises out during this is filtered off with suction, stirred with isopropanol, again filtered off with suction and dried in vacuo.

Workup

  1. temperaturethe reaction mixture is cooled to 0° C
  2. customThe substance which crystallises out during
  3. filtrationthis is filtered off with suction
  4. stirringstirred with isopropanol
  5. filtrationagain filtered off with suction
  6. customdried in vacuo

Sources & evidence

ORD record
ord-2a1bce6f7bc14240b02f8b9d25a1b2c0
Source dataset
uspto-grants-1990_06
Patent number
US04937343

Reaction notes

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