Ammonia → HCID 90024450, compound

HRID 920175Notes

Reaction equation

HRID 920175 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:21])=[C:6]([C@@:8]2([CH3:20])[N:16]=[C:15]([NH2:17])[C:11]3([CH2:14][CH2:13][CH2:12]3)[S:10](=[O:19])(=[O:18])[CH2:9]2)[CH:7]=1.N>CO.[Pd]>[F:21][C:5]1[CH:4]=[CH:3][CH:2]=[CH:7][C:6]=1[C@@:8]1([CH3:20])[N:16]=[C:15]([NH2:17])[C:11]2([CH2:12][CH2:13][CH2:14]2)[S:10](=[O:19])(=[O:18])[CH2:9]1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 86715829HCID 86715829, compound

Product 1

HCID 90024450HCID 90024450, compoundYield 87.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of (R)-7-(5-bromo-2-fluoro-phenyl)-7-methyl-5,5-dioxo-5λ6-thia-8-aza-spiro[3.5]non-8-en-9-ylamine (555 mg, 1.48 mmol, Eq: 1.00) in methanol (50 ml) and ammonia (7 N in MeOH) (634 μl, 4.44 mmol, Eq: 3.0) was added at 23° C. under inert atmosphere Pd/C 10% (157 mg, 148 μmol, Eq: 0.1). The suspension was set under hydrogen (balloon) and stirred at 23° C. for 2 hours. The catalyst was filtered off, washed three times with methanol/dichloromethane (1:1) and evaporated. The residue was extracted with dichloromethane and sat NaHCO3-sol. The organic layer was dried over Na2SO4, filtered and evaporated to give the pure (R)-7-(2-fluoro-phenyl)-7-methyl-5,5-dioxo-5λ6-thia-8-aza-spiro[3.5]non-8-en-9-ylamine (385 mg, 1.3 mmol, 87.8% yield) as a white solid. MS (ISP): m/z=297.5 [M+H]+.

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed three times with methanol/dichloromethane (1:1)
  3. customevaporated
  4. extractionThe residue was extracted with dichloromethane
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-487aa8f9dfd0434daae2b8d796d6eca6
Source dataset
uspto-grants-2016_03
Patent number
US09273042B2

Reaction notes

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