Ethyl Acetate → HCID 21196661, compound

HRID 1066893Notes

Reaction equation

HRID 1066893 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([CH2:12][N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]4[O:24][CH:23]=[CH:22][C:20]4=3)[CH:15]=[N:14]2)[CH2:9]1)=O)(C)(C)C.C([O:27][C:28](=[O:30])[CH3:29])C.[ClH:31].[C:32]([O:35]CC)(=[O:34])[CH3:33]>>[C:28]([OH:27])(=[O:30])/[CH:29]=[CH:33]/[C:32]([OH:35])=[O:34].[Cl:31][CH2:11][CH:10]([CH2:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]3[O:24][CH:23]=[CH:22][C:20]3=2)[CH:15]=[N:14]1)[CH2:9][NH2:8]

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 21196619HCID 21196619, compoundHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 21196661HCID 21196661, compound

Procedure

To an ethyl acetate (10 ml) solution containing 0.46 g of 1-(1-t-butoxycarbonylazetidin-3-ylmethyl)-1H-furo[2,3-g]indazole was added 4 N hydrochloric acid ethyl acetate solution (3 ml), and the resulting mixture was stirred at room temperature for 4 hours. After evaporation of the solvent under a reduced pressure, the residue was extracted with chloroform and washed with 1 N sodium hydroxide and then the thus obtained organic layer was dried with anhydrous sodium sulfate. After removal of the drying agent, the solvent was evaporated and the residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate =5/1) and then treated with fumaric acid in methanol/ethyl acetate to give 0.19 g of 2-chloromethyl-3-(1H-furo[2,3-g]indazol-1-yl)propylamine fumarate.

Workup

  1. customAfter evaporation of the solvent under a reduced pressure
  2. extractionthe residue was extracted with chloroform
  3. washwashed with 1 N sodium hydroxide
  4. dry with materialthe thus obtained organic layer was dried with anhydrous sodium sulfate
  5. customAfter removal of the drying agent
  6. customthe solvent was evaporated
  7. customthe residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate =5/1)
  8. additiontreated with fumaric acid in methanol/ethyl acetate

Sources & evidence

ORD record
ord-864166d7ae114358940cc7bb685791d8
Source dataset
uspto-grants-2001_06
Patent number
US06245796B1

Reaction notes

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