Hydrochloric Acid → HCID 178426333, compound

HRID 641052Notes

Reaction equation

HRID 641052 reaction equation
[CH3:1][N:2]1[C:6]([CH2:7][NH:8][C:9]2[CH:10]=[C:11]([CH:24]=[CH:25][CH:26]=2)[C:12]([C:14]2[CH:22]=[C:21]3[C:17]([CH2:18][C:19](=[O:23])[NH:20]3)=[CH:16][CH:15]=2)=[O:13])=[CH:5][C:4]([CH3:27])=[N:3]1.[CH:28](OCC)=[O:29].[O-]CC.[Na+].Cl>C(O)C>[CH3:1][N:2]1[C:6]([CH2:7][NH:8][C:9]2[CH:10]=[C:11]([CH:24]=[CH:25][CH:26]=2)[C:12]([C:14]2[CH:22]=[C:21]3[C:17]([C:18](=[CH:28][OH:29])[C:19](=[O:23])[NH:20]3)=[CH:16][CH:15]=2)=[O:13])=[CH:5][C:4]([CH3:27])=[N:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8025Ethyl formateHCID 2723922Sodium ethoxideHCID 68699889HCID 68699889, compound

Product 1

HCID 178426333HCID 178426333, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
78 °C

Procedure

6-{3-[(2,5-Dimethyl-2H-pyrazol-3-ylmethyl)-amino]-benzoyl}-1,3-dihydro-indol-2-one (0.100 g, 0.278 mmol) and ethyl formate (0.066 mL, 0.834 mmol) were dissolved in anhydrous ethanol (0.600 mL). The resulting solution was treated in dropwise fashion with a 21 wt % solution of sodium ethoxide in ethanol (0.519 mL, 1.39 mmol). This reaction mixture was heated at 78° C. for 1 h, producing a black oil. 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) causing the formation of a tan precipitate. The suspension was filtered yielding 6-{3-[(2,5-Dimethyl-2H-pyrazol-3-ylmethyl)-amino]-benzoyl}-3-hydroxymethylene-1,3-dihydro-indol-2-one as an orange solid in 42% yield (0.045 g, 0.117 mmol). (prepared below, 0.021 g, 0.056 mmol)

Workup

  1. customproducing a black oil
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationThe suspension was filtered

Sources & evidence

ORD record
ord-4348e6c060f04f508fe6ba05c423fd4e
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Reaction notes

Loading…