Diisopropylethylamine → tert-butyl 4-{[5-cyano-2-(3,5-dichlorophenoxy) phenyl]sulfonyl}-3-(1H-1,2,4-triazol-1-ylmethyl)-1-piperazinecarboxylate

HRID 2242817Notes

Reaction equation

HRID 2242817 reaction equation
[N:1]1([CH2:6][CH:7]2[NH:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8]2)[CH:5]=[N:4][CH:3]=[N:2]1.C(N(C(C)C)CC)(C)C.[C:29]([C:31]1[CH:32]=[CH:33][C:34]([O:41][C:42]2[CH:47]=[C:46]([Cl:48])[CH:45]=[C:44]([Cl:49])[CH:43]=2)=[C:35]([S:37](Cl)(=[O:39])=[O:38])[CH:36]=1)#[N:30]>C1COCC1>[C:29]([C:31]1[CH:32]=[CH:33][C:34]([O:41][C:42]2[CH:47]=[C:46]([Cl:48])[CH:45]=[C:44]([Cl:49])[CH:43]=2)=[C:35]([S:37]([N:12]2[CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8][CH:7]2[CH2:6][N:1]2[CH:5]=[N:4][CH:3]=[N:2]2)(=[O:38])=[O:39])[CH:36]=1)#[N:30]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 592082825-Cyano-2-(3,5-dichlorophenoxy)phenylsulfonylchlorideHCID 59208292tert-butyl 3-(1H-1,2,4-triazol-1-ylmethyl)-1-piperazinecarboxylate

Product 1

HCID 59208297tert-butyl 4-{[5-cyano-2-(3,5-dichlorophenoxy) phenyl]sulfonyl}-3-(1H-1,2,4-triazol-1-ylmethyl)-1-piperazinecarboxylateYield 65.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of tert-butyl 3-(1H-1,2,4-triazol-1-ylmethyl)-1-piperazinecarboxylate (29.5 mg, 0.11 mmol) and di-isopropyl-ethyl amine (28.5 mg, 0.22 mmol) in THF (2 ml) was added 5-cyano-2-(3,5-dichlorophenoxy)benzenesulfonyl chloride (40.0 mg, 0.11 mmol). The mixture was stirred at 50° C. overnight. The solvent was removed and the residue was diluted with CHCl3, washed with sat. NaHCO3 aq. and brine. The organic layer was dried over MgSO4. The solvent was evaporated in vacuo, and the resulting residue was purified by prep. TLC (MeOH/CHCl3= 1/10) to give tert-butyl 4-{[5-cyano-2-(3,5-dichlorophenoxy)phenyl]sulfonyl}-3-(1H-1,2,4-triazol-1-yl methyl)-1-piperazine-carboxylate (42.5 mg, 64.9%): HPLC-MS (ESI): Calcd for C25H26Cl2N6O5S [M+H]+ 593, found: 593.

Workup

  1. customThe solvent was removed
  2. additionthe residue was diluted with CHCl3
  3. washwashed with sat. NaHCO3 aq. and brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. customThe solvent was evaporated in vacuo
  6. customthe resulting residue was purified by prep

Sources & evidence

ORD record
ord-204ebf98686647b6896ebdb791ccf257
Source dataset
uspto-grants-2010_03
Patent number
US07674797B2

Reaction notes

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