Water → (2-Benzenesulfonyl-2,7,8,9-tetrahydro-6-oxo-2-aza-benzo[cd]azulen-8-yl)cyclopropylamine

HRID 25343Notes

Reaction equation

HRID 25343 reaction equation
[C:1]1([S:7]([N:10]2[CH:33]=[C:14]3[CH2:15][CH:16]([N:23]([CH:30]4[CH2:32][CH2:31]4)C(=O)C(F)(F)F)[C:17]4[CH2:18][C:19](=[O:22])[CH:20]=[CH:21][C:12]([C:13]=43)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O>C(O)C>[C:1]1([S:7]([N:10]2[CH:33]=[C:14]3[CH2:15][CH:16]([NH:23][CH:30]4[CH2:31][CH2:32]4)[C:17]4[CH2:18][C:19](=[O:22])[CH:20]=[CH:21][C:12]([C:13]=43)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 962WaterHCID 131724745HCID 131724745, compound

Product 1

HCID 69736436(2-Benzenesulfonyl-2,7,8,9-tetrahydro-6-oxo-2-aza-benzo[cd]azulen-8-yl)cyclopropylamineYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Compound (51) 129 mg was dissolved in ethanol 3 ml. Sodium hydrogenborohydride 42 mg was added to the solution at room temperature and the mixture was stirred for 23 h. Water was added with cooling in ice to the reaction mixture, which was extracted with chloroform. The extracts were washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue obtained was chromatographed on aluminum oxide in chloroform:hexane (1:1) to give the titled compound as a colorless oil, 98 mg. Yield 96%. The titled compound was treated with 1 eq. of oxalic acid to give the salt, which was recrystallized from isopropanol-ether to give colorless crystals, m.p. 119-122° C. (dec.).

Workup

  1. temperaturewith cooling in ice to the reaction mixture, which
  2. extractionwas extracted with chloroform
  3. washThe extracts were washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue obtained
  7. customwas chromatographed on aluminum oxide in chloroform:hexane (1:1)

Sources & evidence

ORD record
ord-cdf608d99796499999eeeaebad0167bb
Source dataset
uspto-grants-2005_02
Patent number
US06858640B2

Reaction notes

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