HCID 178517968, compound → HCID 178507564, compound

HRID 1641313Notes

Reaction equation

HRID 1641313 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:33]=[CH:34][CH:35]=1)[CH2:7][N:8]1[CH2:32][CH2:31][C:11]2([N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)[C:14](=[O:23])[N:13]=[C:12]2[NH:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[CH2:10][CH2:9]1)([O-])=O>CCO>[NH2:1][C:4]1[CH:5]=[C:6]([CH:33]=[CH:34][CH:35]=1)[CH2:7][N:8]1[CH2:32][CH2:31][C:11]2([N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)[C:14](=[O:23])[N:13]=[C:12]2[NH:24][CH:25]2[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]2)[CH2:10][CH2:9]1

Participants

3

Reactant 1

HCID 178517968HCID 178517968, compound

Product 1

HCID 178507564HCID 178507564, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 100 mL EtOH solution of 1.0 g (2.1 mmol) 8-(3-nitrobenzyl)-4-(cyclohexylamino)-1-(3-fluorophenyl)-1,3,8-triazaspiro[4.5]dec-3-en-2-one (example 104) and 0.57 g (2.5 mmol) SnCl2 dihydrate was heated to reflux and allowed to stir overnight. HPLC/MS showed complete conversion so the reaction mixture was filtered through celite washed with EtOH then the filtrate was concentrated. The remaining oil was partitioned between 3N NaOH and EtOAc. A thick white precipitate formed in the aqueous layer. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to pure product.

Workup

  1. temperatureto reflux
  2. filtrationwas filtered through celite
  3. washwashed with EtOH
  4. concentrationthe filtrate was concentrated
  5. customThe remaining oil was partitioned between 3N NaOH and EtOAc
  6. customA thick white precipitate formed in the aqueous layer
  7. washThe organic layer was washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated to pure product

Sources & evidence

ORD record
ord-057ccbe7477f436583e6e7cc9963e9f8
Source dataset
uspto-grants-2012_02
Patent number
US08114887B2

Reaction notes

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