Hydrochloric Acid → HCID 16222738, compound

HRID 2416630Notes

Reaction equation

HRID 2416630 reaction equation
C([O:4][C@@:5]1([CH2:40][CH3:41])[C:37]2[CH:36]=[C:35]3[N:11]([CH2:12][C:13]4[C:14]3=[N:15][C:16]3[C:17]5[C:18]=4[N:19]([CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C:20]([C:26]([F:29])([F:28])[F:27])=[N:21][C:22]=5[CH:23]=[CH:24][CH:25]=3)[C:10](=[O:38])[C:9]=2[CH2:8][O:7][C:6]1=[O:39])(=O)C.NN.Cl>CO>[CH2:40]([C@:5]1([OH:4])[C:37]2[CH:36]=[C:35]3[N:11]([CH2:12][C:13]4[C:14]3=[N:15][C:16]3[C:17]5[C:18]=4[N:19]([CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C:20]([C:26]([F:29])([F:28])[F:27])=[N:21][C:22]=5[CH:23]=[CH:24][CH:25]=3)[C:10](=[O:38])[C:9]=2[CH2:8][O:7][C:6]1=[O:39])[CH3:41]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9321HydrazineHCID 21054602HCID 21054602, compound

Product 1

HCID 16222738HCID 16222738, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a cold (0° C.) stirred solution of (9S)-9-acetoxy-9-ethyl-1-pentyl-2-trifluoromethyl-1H,12H-pyrano[3″,4″:6′,7′]indolizino[1′,2′:6,5]pyrido[4,3,2-de]quinazoline-10,13(9H,15H)-dione (105 mg, 0.18 mmol) in MeOH (15 ml) was added anhydrous hydrazine (0.29 ml, 9.00 mmol). After being stirred at room temperature for 2 hr., the mixture was acidified with 10% HCl solution in MeOH at 0° C. and stirred at room temperature for 2 h. The mixture was filtered and washed with CH2Cl2. After the combined filtrate and washings were concentrated under reduced pressure, the residue was suspended in CH2Cl2 (30 ml). The mixture was filtered and washed with CH2Cl2. The combined filtrate and washings were concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane/methanol=40/1-20/1) to give pure product (74.0 mg, 76%).

Workup

  1. stirringstirred at room temperature for 2 h
  2. filtrationThe mixture was filtered
  3. washwashed with CH2Cl2
  4. concentrationAfter the combined filtrate and washings were concentrated under reduced pressure
  5. filtrationThe mixture was filtered
  6. washwashed with CH2Cl2
  7. concentrationThe combined filtrate and washings were concentrated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel (dichloromethane/methanol=40/1-20/1)

Sources & evidence

ORD record
ord-3769fd7227204d8b9024d5bb67dc5652
Source dataset
uspto-grants-2004_11
Patent number
US06825194B2

Reaction notes

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