4-(Tert-butylcarbamoyl)-2-methoxybenzenesulphonyl chloride → N-tert-Butyl-4-{[3-(4-chlorophenyl)-5-oxo-4-prop-2-en-1-yl-4,5-dihydro-1H-1,2,4-triazol-1-yl]sulphonyl}-3-methoxybenzenecarboxamide

HRID 536549Notes

Reaction equation

HRID 536549 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:14][CH:15]=[CH2:16])[C:10](=[O:13])[NH:11][N:12]=2)=[CH:4][CH:3]=1.CC([O-])(C)C.[K+].[C:23]([NH:27][C:28]([C:30]1[CH:35]=[CH:34][C:33]([S:36](Cl)(=[O:38])=[O:37])=[C:32]([O:40][CH3:41])[CH:31]=1)=[O:29])([CH3:26])([CH3:25])[CH3:24]>O1CCCC1>[C:23]([NH:27][C:28]([C:30]1[CH:35]=[CH:34][C:33]([S:36]([N:11]2[C:10](=[O:13])[N:9]([CH2:14][CH:15]=[CH2:16])[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)=[N:12]2)(=[O:37])=[O:38])=[C:32]([O:40][CH3:41])[CH:31]=1)=[O:29])([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 99265364-(Tert-butylcarbamoyl)-2-methoxybenzenesulphonyl chlorideHCID 23665647Potassium tert-butoxideHCID 497656025-(4-chlorophenyl)-4-allyl-2,4-dihydro-3H-1,2,4-triazol-3-one

Product 1

HCID 46238665N-tert-Butyl-4-{[3-(4-chlorophenyl)-5-oxo-4-prop-2-en-1-yl-4,5-dihydro-1H-1,2,4-triazol-1-yl]sulphonyl}-3-methoxybenzenecarboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

An amount of 231 mg (0.24 mmol) of the compound from Example 3A was suspended in 4 ml of tetrahydrofuran and cooled to −78° C. This suspension was admixed with stirring with 110 mg (0.981 mmol) of potassium tert-butylate. The mixture was allowed to warm to room temperature, and the solid dissolved. The reaction solution was stirred at room temperature for 10 minutes thereafter. Subsequently it was cooled again to −78° C. It was admixed with 300 mg (0.981 mmol) of 4-(tert-butylcarbamoyl)-2-methoxybenzenesulphonyl chloride (illustration as per Liotta et al., J. Org. Chem., 2001, 66, 3653-3661), the cooling bath was removed, and the solution was left with further stirring at room temperature overnight. The residue was admixed with water. It was extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulphate and freed from the solvent on a rotary evaporator. The residue was purified by preparative HPLC (Method 6). This gave 275 mg (55% of theory) of the target compound.

Workup

  1. temperatureto warm to room temperature
  2. dissolutionthe solid dissolved
  3. temperatureSubsequently it was cooled again to −78° C
  4. customthe cooling bath was removed
  5. waitthe solution was left
  6. stirringwith further stirring at room temperature overnight
  7. extractionIt was extracted twice with ethyl acetate
  8. dry with materialThe combined organic phases were dried over sodium sulphate
  9. customfreed from the solvent on a rotary evaporator
  10. customThe residue was purified by preparative HPLC (Method 6)

Sources & evidence

ORD record
ord-470535b253ca4a81a0586345f8fc7c77
Source dataset
uspto-grants-2014_10
Patent number
US08859601B2

Reaction notes

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