Hydrochloric Acid → HCID 16224669, compound

HRID 2214464Notes

Reaction equation

HRID 2214464 reaction equation
C([O:4][C@@:5]1([CH2:41][CH3:42])[C:38]2[CH:37]=[C:36]3[N:11]([CH2:12][C:13]4[C:14]3=[N:15][C:16]3[C:17]5[C:18]=4[N:19]([CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:20]([CH2:26][O:27]C(=O)C)=[N:21][C:22]=5[CH:23]=[CH:24][CH:25]=3)[C:10](=[O:39])[C:9]=2[CH2:8][O:7][C:6]1=[O:40])(=O)C.NN.Cl>CO>[CH2:41]([C@:5]1([OH:4])[C:38]2[CH:37]=[C:36]3[N:11]([CH2:12][C:13]4[C:14]3=[N:15][C:16]3[C:17]5[C:18]=4[N:19]([CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:20]([CH2:26][OH:27])=[N:21][C:22]=5[CH:23]=[CH:24][CH:25]=3)[C:10](=[O:39])[C:9]=2[CH2:8][O:7][C:6]1=[O:40])[CH3:42]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9321HydrazineHCID 21054589HCID 21054589, compound

Product 1

HCID 16224669HCID 16224669, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (9S)-9-acetoxy-2-acetoxymethyl-9-ethyl-1-pentyl-1H,12H-pyrano[3″,4″:6′7′]indolizino[1′2′:6,5]pyrido[4,3,2-de]quinazoline-10,13(9H,15H)-dione (34 mg, 0.059 mmol) in methanol (3 ml) cooled in an ice-bath was added anhydrous hydrazine (100 μl) and the mixture was stirred for 2 hr. at room temperature. Aqueous 1 N hydrochloric acid solution (5 ml) was added dropwise to acidify the reaction mixture, and the mixture was stirred for 1 hr. at room temperature. The mixture was extracted with dichloromethane (50 ml) and the dichloromethane layer was washed with brine, dried over MgSO4 and evaporated. The residue was purified by column chromatography (dichloromethane/methanol=25/1) to give pure product (19 mg, 65%).

Workup

  1. customat room temperature
  2. stirringthe mixture was stirred for 1 hr
  3. customat room temperature
  4. extractionThe mixture was extracted with dichloromethane (50 ml)
  5. washthe dichloromethane layer was washed with brine
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. customThe residue was purified by column chromatography (dichloromethane/methanol=25/1)

Sources & evidence

ORD record
ord-be515a916b464942b4d076a6af60ad70
Source dataset
uspto-grants-2006_09
Patent number
US07109195B2

Reaction notes

Loading…