Hydrochloric Acid → HCID 178428619, compound

HRID 2116796Notes

Reaction equation

HRID 2116796 reaction equation
[CH3:1][N:2]1[C:6]([NH:7][C:8](=[O:26])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15][C:16]2[CH:24]=[C:23]3[C:19]([CH2:20][C:21](=[O:25])[NH:22]3)=[CH:18][CH:17]=2)=[CH:5][C:4]([CH3:27])=[N:3]1.[CH:28](OCC)=[O:29].[O-]CC.[Na+].Cl>C(O)C.CCOC(C)=O>[CH3:1][N:2]1[C:6]([NH:7][C:8](=[O:26])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15][C:16]2[CH:24]=[C:23]3[C:19](/[C:20](=[CH:28]/[OH:29])/[C:21](=[O:25])[NH:22]3)=[CH:18][CH:17]=2)=[CH:5][C:4]([CH3:27])=[N:3]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8025Ethyl formateHCID 2723922Sodium ethoxideHCID 69128941N-(2,5-Dimethyl-2H-pyrazol-3-yl)-2-(2-oxo-2,3-dihydro-1H-indol-6-ylsulfanyl)-benzamide

Product 1

HCID 178428619HCID 178428619, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
78 °C

Procedure

N-(2,5-Dimethyl-2H-pyrazol-3-yl)-2-(2-oxo-2,3-dihydro-1H-indol-6-ylsulfanyl)-benzamide (as prepared above in Step 4; 0.300 g, 0.793 mmol) was dissolved in anhydrous ethanol (8 mL) and the resulting solution was treated with ethyl formate (0.058 mL, 0.717 mmol) The resulting solution was treated in dropwise fashion with a 21 wt % solution of sodium ethoxide in ethanol (1.48 mL, 3.97 mmol). This reaction mixture was heated at 78° C. for 0.5 h, which caused the reaction mixture to turn black in color. Subsequently, the reaction mixture was cooled to room temperature, and then the reaction pH was adjusted to pH=1 with dropwise addition of 1M HCl(aq). The reaction mixture was diluted with EtOAc (25 mL) and extracted with brine (2×25 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified via flash silica gel chromatography (5% MeOH in CHCl3) affording the title compound in 19% yield (0.061 g, 0.150 mmol).

Workup

  1. temperatureSubsequently, the reaction mixture was cooled to room temperature
  2. extractionextracted with brine (2×25 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified via flash silica gel chromatography (5% MeOH in CHCl3)

Sources & evidence

ORD record
ord-1984ca10c1dd4f719a6c315e13e05f91
Source dataset
uspto-grants-2008_10
Patent number
US07439371B2

Reaction notes

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