2-Hydrazinoethanol → HCID 22063987, compound

HRID 1828193Notes

Reaction equation

HRID 1828193 reaction equation
[CH:1]1([N:5]2[C:9]3[CH:10]=[CH:11][C:12]([CH:14]([C:17](=O)[C:18]4[CH:19]=[C:20]([CH3:24])[CH:21]=[CH:22][CH:23]=4)[C:15]#[N:16])=[CH:13][C:8]=3[N:7]([CH3:26])[C:6]2=[O:27])[CH2:4][CH2:3][CH2:2]1.[OH:28][CH2:29][CH2:30][NH:31][NH2:32].C(=O)(O)[O-].[Na+]>CC(O)C.C(O)(=O)C>[NH2:16][C:15]1[N:31]([CH2:30][CH2:29][OH:28])[N:32]=[C:17]([C:18]2[CH:19]=[C:20]([CH3:24])[CH:21]=[CH:22][CH:23]=2)[C:14]=1[C:12]1[CH:11]=[CH:10][C:9]2[N:5]([CH:1]3[CH2:4][CH2:3][CH2:2]3)[C:6](=[O:27])[N:7]([CH3:26])[C:8]=2[CH:13]=1

Participants

6

Reactant 3

HCID 80172-HydrazinoethanolHCID 516892Sodium BicarbonateHCID 220639752-(1-Cyclobutyl-3-methyl-2-oxo-2,3-dihydro-1H-benzoimidazol-5-yl)-3-oxo-3-m-tolyl-propionitrile

Product 1

HCID 22063987HCID 22063987, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
70 °C

Procedure

2-(1-Cyclobutyl-3-methyl-2-oxo-2,3-dihydro-1H-benzoimidazol-5-yl)-3-oxo-3-m-tolyl-propionitrile (66.5 mg, 0.19 mmol) was diluted with 2-propanol (0.4 mL) and acetic acid (0.8 mL). Hydroxyethyl hydrazine was then added (0.1 mL) and the mixture was heated to 70° C. for 8 hours. The reaction was cooled, poured onto saturated sodium bicarbonate and extracted with ethyl acetate. The organic layer was dried with sodium sulfate and concentrated. Preparative thin layer chromatography gave 5-[5-Amino-1-(2-hydroxy-ethyl)-3-m-tolyl-1H-pyrazol-4-yl]-1-cyclobutyl-3-methyl-1,3-dihydro-benzoimidazol-2-one (27.6 mg).

Workup

  1. temperatureThe reaction was cooled
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bdb1aec47dbc449daf794369a7bdfc5e
Source dataset
uspto-grants-2006_06
Patent number
US07056918B2

Reaction notes

Loading…