Hydrochloric Acid → HCID 67041131, compound

HRID 2416631Notes

Reaction equation

HRID 2416631 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]([CH2:29][CH:30]([CH3:32])[CH3:31])[C:20]([N:26]([CH3:28])[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.[ClH:42]>CO.O1CCOCC1>[ClH:42].[CH3:28][N:26]([CH3:27])[C:20]1[N:19]([CH2:29][CH:30]([CH3:31])[CH3:32])[C:18]2=[C:13]3[CH2:12][N:11]4[C:33](=[CH:34][C:35]5[C@:5]([CH2:38][CH3:39])([OH:4])[C:6](=[O:37])[O:7][CH2:8][C:9]=5[C:10]4=[O:36])[C:14]3=[N:15][C:16]3[C:17]2=[C:22]([CH:23]=[CH:24][CH:25]=3)[N:21]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 9321HydrazineHCID 69034192HCID 69034192, compound

Product 1

HCID 67041131HCID 67041131, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a solution of (9S)-9-acetoxy-2-(dimethylamino)-9-ethyl-1-(2-methylpropyl)-1H,12H-pyrano[3″,4″:6′,7′]indolizino[1′,2′:6,5]pyrido[4,3,2-de]quinazoline-10,13(9H,15H)-dione (8.7 mg, 0.023 mmol) in methanol (2 ml) and 1,4-dioxane(2 ml) cooled in an ice-bath was added anhydrous hydrazine (100 μl). The mixture was warmed to room temperature and stirred for 3 hr. 10% HCl in methanol was added dropwise to acidify the reaction mixture and the mixture was stirred at room temperature for 2 h. After concentrated under reduced pressure, the obtaining residue was purified by reversed phase column chromatography (water/methanol=1/0−1/2) to give the product (7.4 mg, 85%) as a yellow powder.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 h
  2. concentrationAfter concentrated under reduced pressure
  3. customthe obtaining residue was purified by reversed phase column chromatography (water/methanol=1/0−1/2)

Sources & evidence

ORD record
ord-5a5fc93915c949b69e975411483fb41b
Source dataset
uspto-grants-2004_11
Patent number
US06825194B2

Reaction notes

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