Hydrochloric Acid → HCID 21054582, compound

HRID 2416625Notes

Reaction equation

HRID 2416625 reaction equation
C([O:4][C@@:5]1([CH2:36][CH3:37])[C:33]2[CH:32]=[C:31]3[N:11]([CH2:12][C:13]4[C:14]3=[N:15][C:16]3[C:17]5[C:18]=4[N:19]([CH2:27][CH2:28][CH2:29][CH3:30])[C:20](=[O:26])[NH:21][C:22]=5[CH:23]=[CH:24][CH:25]=3)[C:10](=[O:34])[C:9]=2[CH2:8][O:7][C:6]1=[O:35])(=O)C.NN.Cl>CO>[CH2:27]([N:19]1[C:18]2=[C:13]3[CH2:12][N:11]4[C:31](=[CH:32][C:33]5[C@:5]([CH2:36][CH3:37])([OH:4])[C:6](=[O:35])[O:7][CH2:8][C:9]=5[C:10]4=[O:34])[C:14]3=[N:15][C:16]3[C:17]2=[C:22]([CH:23]=[CH:24][CH:25]=3)[NH:21][C:20]1=[O:26])[CH2:28][CH2:29][CH3:30]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9321HydrazineHCID 21054585HCID 21054585, compound

Product 1

HCID 21054582HCID 21054582, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (9S)-9-acetoxy-1-butyl-9-ethyl-1H,12H-pyrano[3″,4″:6′,7′]indolizino-[1′,2′:6,5]pyrido[4,3,2-de]quinazoline-2,10,13(3H,9H,15H)-trione (11.5 mg, 0.023 mmol) in MeOH (3 ml) cooled in an ice-bath was added anhydrous hydrazine (100 μl). The mixture was warmed to room temperature and stirred for 1 hr. Aqueous 1 N HCl solution was added dropwise to acidify the reaction mixture and the mixture was stirred for 1 hr. at room temperature. After concentrated under reduced pressure, the obtaining residue was extracted with CH2Cl2 (20 ml×3). The combined CH2Cl2 solution was washed with brine, dried over MgSO4 and evaporated. The residue was purified by column chromatography (dichloromethane/methanol=30/1) to give pure product (6.1 mg, 58%).

Workup

  1. stirringthe mixture was stirred for 1 hr
  2. customat room temperature
  3. concentrationAfter concentrated under reduced pressure
  4. extractionthe obtaining residue was extracted with CH2Cl2 (20 ml×3)
  5. washThe combined CH2Cl2 solution was washed with brine
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. customThe residue was purified by column chromatography (dichloromethane/methanol=30/1)

Sources & evidence

ORD record
ord-cfe24ca18f5940e49b3cd38787fdd187
Source dataset
uspto-grants-2004_11
Patent number
US06825194B2

Reaction notes

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