Sulfuric Acid → HCID 58066682, compound

HRID 390418Notes

Reaction equation

HRID 390418 reaction equation
[C:1]([S:5][CH2:6][C:7]1[CH:8]=[C:9]([NH:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])[CH:10]=[CH:11][C:12]=1[CH2:13][N:14]1[CH:18]=[C:17]([CH2:19][C:20]#N)[CH:16]=[N:15]1)([CH3:4])([CH3:3])[CH3:2].S(=O)(=O)(O)[OH:30].[C:34](Cl)(=[O:36])[CH3:35]>CCO.S(=O)(=O)(O)O.O>[CH2:34]([O:36][C:20](=[O:30])[CH2:19][C:17]1[CH:16]=[N:15][N:14]([CH2:13][C:12]2[CH:11]=[CH:10][C:9]([NH:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:8][C:7]=2[CH2:6][S:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH:18]=1)[CH3:35]

Participants

7

Reactant 3

HCID 1118Sulfuric AcidHCID 6367Acetyl chlorideHCID 58066681HCID 58066681, compound

Product 1

HCID 58066682HCID 58066682, compound

Reagents, catalysts & solvents 3

HCID 1118Sulfuric AcidCatalystHCID 702EthanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

N-[3-tert-Butylsulfanylmethyl-4-(4-cyanomethyl-pyrazol-1-ylmethyl)-phenyl]-2,2-dimethyl-propionamide (0.080 g, 0.20 mmol) in EtOH (10 mL) was treated with sulfuric acid (10 drops) and stirred at 50° C. for 2 hours. No reaction was observed, so additional sulfuric acid (0.5 mL) was added, and the reaction was stirred at 62° C. overnight. A small amount of product was observed, so the mixture was diluted with H2O and extracted with EtOAc to isolate a mixture of starting material and product. The mixture was dissolved in EtOH (10 mL) and treated with acetyl chloride (0.29 mL, 4.0 mmol). The reaction was stirred overnight at 62° C., after which time the reaction was complete. The mixture was partitioned between EtOAc and H2O, and the organic layer was separated and purified by preparative HPLC to give the title compound.

Workup

  1. stirringthe reaction was stirred at 62° C. overnight
  2. extractionextracted with EtOAc
  3. customto isolate
  4. additiona mixture of starting material and product
  5. stirringThe reaction was stirred overnight at 62° C.
  6. customThe mixture was partitioned between EtOAc and H2O
  7. customthe organic layer was separated
  8. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-d1064b2ff6cd4615b40dac4d06c3232b
Source dataset
uspto-grants-2013_02
Patent number
US08383654B2

Reaction notes

Loading…