Hydrochloric Acid → HCID 69034165, compound

HRID 2416628Notes

Reaction equation

HRID 2416628 reaction equation
C([O:4][C@@:5]1([CH2:45][CH3:46])[C:42]2[CH:41]=[C:40]3[N:11]([CH2:12][C:13]4[C:14]3=[N:15][C:16]3[C:17]5[C:18]=4[N:19]([CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[C:20]([CH2:26][NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[N:21][C:22]=5[CH:23]=[CH:24][CH:25]=3)[C:10](=[O:43])[C:9]=2[CH2:8][O:7][C:6]1=[O:44])(=O)C.NN.Cl>CO>[C:31]([O:30][C:28]([NH:27][CH2:26][C:20]1[N:19]([CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[C:18]2=[C:13]3[CH2:12][N:11]4[C:40](=[CH:41][C:42]5[C@:5]([CH2:45][CH3:46])([OH:4])[C:6](=[O:44])[O:7][CH2:8][C:9]=5[C:10]4=[O:43])[C:14]3=[N:15][C:16]3[C:17]2=[C:22]([CH:23]=[CH:24][CH:25]=3)[N:21]=1)=[O:29])([CH3:32])([CH3:33])[CH3:34]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9321HydrazineHCID 69033045HCID 69033045, compound

Product 1

HCID 69034165HCID 69034165, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (9S)-9-acetoxy-2-(t-butoxycarbonylamino)methyl-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 (56 mg, 0.089 mmol) in methanol (2 ml) cooled in an ice-bath was added anhydrous hydrazine (50 μl) and the mixture was stirred for 1 hr. at room temperature. Concentrated hydrochloric acid solution (0.3 ml) was added dropwise to the reaction mixture with cooling in an ice-bath, and the mixture was stirred for 1 hr. at room temperature. The mixture was concentrated under reduced pressure. The residue was purified by column chromatography (dichloromethane/methanol=25/1) to give pure product (33 mg, 63%).

Workup

  1. customat room temperature
  2. temperaturewith cooling in an ice-bath
  3. stirringthe mixture was stirred for 1 hr
  4. customat room temperature
  5. concentrationThe mixture was concentrated under reduced pressure
  6. customThe residue was purified by column chromatography (dichloromethane/methanol=25/1)

Sources & evidence

ORD record
ord-375c1dae58ac4193bf85b5a1e62a7038
Source dataset
uspto-grants-2004_11
Patent number
US06825194B2

Reaction notes

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