Hydrazine hydrate (1:1) → HCID 178489264, compound

HRID 2037190Notes

Reaction equation

HRID 2037190 reaction equation
O[C:2]1[C:3](=[O:37])[N:4]([C:26]2[CH:31]=[CH:30][C:29]([C:32]3[CH:36]=[CH:35][S:34][CH:33]=3)=[CH:28][CH:27]=2)[CH:5]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][CH3:25])[C:6]=1[C:7]([C:9]1([CH3:17])[CH2:14][O:13]C(C)(C)[O:11][CH2:10]1)=O.O.[NH2:39][NH2:40].Cl.CO>C(O)(=O)C>[OH:11][CH2:10][C:9]([C:7]1[C:6]2[CH:5]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][CH3:25])[N:4]([C:26]3[CH:27]=[CH:28][C:29]([C:32]4[CH:36]=[CH:35][S:34][CH:33]=4)=[CH:30][CH:31]=3)[C:3](=[O:37])[C:2]=2[NH:39][N:40]=1)([CH2:14][OH:13])[CH3:17]

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 21893726Hydrochloride methanolHCID 58365702HCID 58365702, compound

Product 1

HCID 178489264HCID 178489264, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3-hydroxy-4-(2,2,5-trimethyl-1,3-dioxane5-yl)carbonyl-5-(2-methoxyphenyl)-1-(4-thiophene-3-ylphenyl)-1,5-dihydropyrrole-2-one (0.15 g, 0.3 mmol), hydrazine hydrate (0.07 mL, 1.4 mmol) and acetic acid (1 mL) was heated at reflux overnight. After the reaction mixture was concentrated in vacuo, to the resulting residue was added 2 mol/L hydrochloric acid/methanol solution (2.89 mL, 5.8 mmol) and the resulting mixture was heated at reflux for 6 hours. After the reaction mixture was concentrated in vacuo, saturated sodium bicarbonate solution was added to the residue and the mixture was extracted with chloroform. The extract was dried over anhydrous magnesium sulfate and concentrated in vacuo. The resulting residue was purified on a silica gel column chromatography (methanol/chloroform). The resulting compound was triturated with ethyl acetate and n-hexane to give 3-(1,1-dihydroxymethylethyl) 4-(2-methoxyphenyl)-5-(4-thiophene-3-ylphenyl)-4,5-dihydro-1H-pyrrolo[3,4-c]pyrazole-6-one (0.105 g, yield: 77%) as colorless solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. concentrationAfter the reaction mixture was concentrated in vacuo, to the resulting residue
  4. temperaturethe resulting mixture was heated
  5. temperatureat reflux for 6 hours
  6. concentrationAfter the reaction mixture was concentrated in vacuo, saturated sodium bicarbonate solution
  7. additionwas added to the residue
  8. extractionthe mixture was extracted with chloroform
  9. dry with materialThe extract was dried over anhydrous magnesium sulfate
  10. concentrationconcentrated in vacuo
  11. customThe resulting residue was purified on a silica gel column chromatography (methanol/chloroform)
  12. customThe resulting compound was triturated with ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-8266d74b657340b4941d2d8b00041c8c
Source dataset
uspto-grants-2013_11
Patent number
US08575197B2

Reaction notes

Loading…