Hydrochloric Acid → HCID 16222739, compound

HRID 2416632Notes

Reaction equation

HRID 2416632 reaction equation
C([O:4][C@@:5]1([CH2:38][CH3:39])[C:35]2[CH:34]=[C:33]3[N:11]([CH2:12][C:13]4[C:14]3=[N:15][C:16]3[C:17]5[C:18]=4[N:19]([CH2:28][CH2:29][CH:30]([CH3:32])[CH3:31])[C:20]([S:26][CH3:27])=[N:21][C:22]=5[CH:23]=[CH:24][CH:25]=3)[C:10](=[O:36])[C:9]=2[CH2:8][O:7][C:6]1=[O:37])(=O)C.NN.Cl>CO.O1CCOCC1>[CH2:38]([C@:5]1([OH:4])[C:35]2[CH:34]=[C:33]3[N:11]([CH2:12][C:13]4[C:14]3=[N:15][C:16]3[C:17]5[C:18]=4[N:19]([CH2:28][CH2:29][CH:30]([CH3:32])[CH3:31])[C:20]([S:26][CH3:27])=[N:21][C:22]=5[CH:23]=[CH:24][CH:25]=3)[C:10](=[O:36])[C:9]=2[CH2:8][O:7][C:6]1=[O:37])[CH3:39]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 9321HydrazineHCID 69037086HCID 69037086, compound

Product 1

HCID 16222739HCID 16222739, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a solution of (9S)-9-acetoxy-9-ethyl-1-(3-methylbutyl)-2-methylthio-1H,12H-pyrano[3″,4″:6′,7′]indolizino[1′,2′:6,5]pyrido[4,3,2-de]quinazoline-10,13(9H,15H)-dione (43.0 mg, 0.08 mmol) in methanol (2 ml) and 1,4-dioxane (2 ml) was added anhydrous hydrazine (200 μl). The mixture was stirred at room temperature for 2.5 hr. 10% HCl in methanol was added dropwise to acidify the reaction mixture and the mixture was stirred at room temperature for 2 hr. After concentrated under reduced pressure, the obtaining residue was partitioned between dichloromethane and water. The organic layer was concentrated under reduced pressure. The residue was purified by column chromatography (dichloromethane/methanol=100/1) to give the product (33.2 mg, 84%) as an orange powder.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hr
  2. concentrationAfter concentrated under reduced pressure
  3. customthe obtaining residue was partitioned between dichloromethane and water
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customThe residue was purified by column chromatography (dichloromethane/methanol=100/1)

Sources & evidence

ORD record
ord-3f6bf5e7ae664649b25a663b0dd45ed2
Source dataset
uspto-grants-2004_11
Patent number
US06825194B2

Reaction notes

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