Ammonia → HCID 71532169, compound

HRID 920173Notes

Reaction equation

HRID 920173 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:22])=[C:6]([C@@:8]2([CH3:21])[N:17]=[C:16]([NH2:18])[C:11]3([CH2:15][CH:14]=[CH:13][CH2:12]3)[S:10](=[O:20])(=[O:19])[CH2:9]2)[CH:7]=1.N>CO.[Pd]>[F:22][C:5]1[CH:4]=[CH:3][CH:2]=[CH:7][C:6]=1[C@@:8]1([CH3:21])[N:17]=[C:16]([NH2:18])[C:11]2([CH2:12][CH2:13][CH2:14][CH2:15]2)[S:10](=[O:20])(=[O:19])[CH2:9]1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 90025129(R)-8-(5-bromo-2-fluoro-phenyl)-8-methyl-6,6-dioxo-6lambda6-thia-9-aza-spiro[4.5]deca-2,9-dien-10-ylamine

Product 1

HCID 71532169HCID 71532169, compoundYield 89.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of (R)-8-(5-bromo-2-fluoro-phenyl)-8-methyl-6,6-dioxo-6λ6-thia-9-aza-spiro[4.5]deca-2,9-dien-10-ylamine (245 mg, 633 μmol, Eq: 1.00) in methanol (10 ml) and ammonia (7 N in MeOH) (271 μl, 1.9 mmol, Eq: 3.0) was added at 23° C. under inert atmosphere Pd/C 10% (67.3 mg, 63.3 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 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)-8-(2-fluoro-phenyl)-8-methyl-6,6-dioxo-6λ6-thia-9-aza-spiro[4.5]dec-9-en-10-ylamine (175 mg, 564 μmol, 89.1% yield) as a white solid. MS (ISP): m/z=311.5 [M+H]+.

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed three times with methanol
  3. customevaporated
  4. extractionThe residue was extracted with dichloromethane and sat. NaHCO3-sol
  5. dry with material, the organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-2616c27328f44709aeb2723072d2be22
Source dataset
uspto-grants-2016_03
Patent number
US09273042B2

Reaction notes

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