Hydrochloric Acid → HCID 16222524, compound

HRID 2214463Notes

Reaction equation

HRID 2214463 reaction equation
C([O:4][C@@:5]1([CH2:35][CH3:36])[C:32]2[CH:31]=[C:30]3[N:11]([CH2:12][C:13]4[C:14]3=[N:15][C:16]3[C:17]5[C:18]=4[N:19]([CH2:26][CH2:27][CH2:28][CH3:29])[CH:20]=[N:21][C:22]=5[CH:23]=[CH:24][CH:25]=3)[C:10](=[O:33])[C:9]=2[CH2:8][O:7][C:6]1=[O:34])(=O)C.NN.Cl>CO>[CH2:26]([N:19]1[C:18]2=[C:13]3[CH2:12][N:11]4[C:30](=[CH:31][C:32]5[C@:5]([CH2:35][CH3:36])([OH:4])[C:6](=[O:34])[O:7][CH2:8][C:9]=5[C:10]4=[O:33])[C:14]3=[N:15][C:16]3[C:17]2=[C:22]([CH:23]=[CH:24][CH:25]=3)[N:21]=[CH:20]1)[CH2:27][CH2:28][CH3:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9321HydrazineHCID 69033437HCID 69033437, compound

Product 1

HCID 16222524HCID 16222524, compoundYield 70%

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-10,13(9H,15H)-dione (6.1 mg, 0.013 mmol) in MeOH (2 ml) cooled in an ice-bath was added anhydrous hydrazine (100 μl) and the mixture was stirred for 1 hr. at room temperature. 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 residue was extracted with CH2Cl2 (30 ml) and the CH2Cl2 solution was washed with brine, dried over MgSO4 and evaporated. The residue was purified by column chromatography (dichloromethane/methanol=20/1) to give pure product (3.9 mg, 70%).

Workup

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

Sources & evidence

ORD record
ord-0f91e378a5324f108e3a34932e169801
Source dataset
uspto-grants-2006_09
Patent number
US07109195B2

Reaction notes

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