Pyridine, 1,2,3,6-tetrahydro-4-[4-(trifluoromethyl)phenyl]- → 7-(4-(Trifluoromethoxy)phenyl)-3-thia-7,9-diazabicyclo[3.3.1]nonane-6,8-dione

HRID 2110163Notes

Reaction equation

HRID 2110163 reaction equation
C([N:8]1[CH:13]2[C:14](=[O:29])[N:15]([C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=3)[C:16](=[O:17])[CH:9]1[CH2:10][S:11][CH2:12]2)C1C=CC=CC=1.FC(F)(F)C1C=CC(C2CCNCC=2)=CC=1>[OH-].[OH-].[Pd+2].CO>[F:28][C:25]([F:26])([F:27])[O:24][C:21]1[CH:20]=[CH:19][C:18]([N:15]2[C:16](=[O:17])[CH:9]3[NH:8][CH:13]([CH2:12][S:11][CH2:10]3)[C:14]2=[O:29])=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 12440708Pyridine, 1,2,3,6-tetrahydro-4-[4-(trifluoromethyl)phenyl]-HCID 689644339-Benzyl-7-(4-(trifluoromethoxy)phenyl)-3-thia-7,9-diazabicyclo[3.3.1]nonane-6,8-dione

Product 1

HCID 689586847-(4-(Trifluoromethoxy)phenyl)-3-thia-7,9-diazabicyclo[3.3.1]nonane-6,8-dione

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalyst2×HCID 887MethanolSolvent

Procedure

A mixture of 9-benzyl-7-(4-(trifluoromethoxy)phenyl)-3-thia-7,9-diazabicyclo[3.3.1]nonane-6,8-dione (143 mg, 0.34 mmol), 20% Pd(OH)2/C (243 mg, 0.35 mmol Pd), methanol (10 mL), and 1N HCl (3 mL) were shaken under 60 psi of H2. After 16 h, more 20% Pd(OH)2/C (250 mg, 0.36 mmol Pd) was added, and the reaction was shaken under 90 psi of H2. After an additional 24 h, the reaction was filtered through Celite, concentrated, and then partitioned between ethyl acetate (50 mL) and sat'd NaHCO3 (50 mL). The organic extract was dried, filtered, concentrated, and purified by silica gel chromatography (2:3→0:1; hexanes:ethyl acetate) to give 7-(4-(trifluoromethoxy)phenyl)-3-thia-7,9-diazabicyclo[3.3.1]nonane-6,8-dione: MS (ESI): 333.4 (M+H).

Workup

  1. stirringthe reaction was shaken under 90 psi of H2
  2. waitAfter an additional 24 h
  3. filtrationthe reaction was filtered through Celite
  4. concentrationconcentrated
  5. custompartitioned between ethyl acetate (50 mL) and sat'd NaHCO3 (50 mL)
  6. extractionThe organic extract
  7. customwas dried
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified by silica gel chromatography (2:3→0:1; hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-33e570146f6f4a37b70a64f9255bfd6e
Source dataset
uspto-grants-2009_04
Patent number
US07517884B2

Reaction notes

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