Ammonia → HCID 90025129, compound

HRID 920172Notes

Reaction equation

HRID 920172 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:22])=[C:6]([C@@:8]2([CH3:21])[NH:17][C:16](=S)[C:11]3([CH2:15][CH:14]=[CH:13][CH2:12]3)[S:10](=[O:20])(=[O:19])[CH2:9]2)[CH:7]=1.[NH3:23]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:22])=[C:6]([C@@:8]2([CH3:21])[N:17]=[C:16]([NH2:23])[C:11]3([CH2:15][CH:14]=[CH:13][CH2:12]3)[S:10](=[O:20])(=[O:19])[CH2:9]2)[CH:7]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 90025491(R)-8-(5-bromo-2-fluoro-phenyl)-8-methyl-6,6-dioxo-6lambda6-thia-9-aza-spiro[4.5]dec-2-en-10-thione

Product 1

HCID 90025129HCID 90025129, compoundYield 86.7%

Conditions

Temperature
60 °C

Procedure

A mixture of (R)-8-(5-bromo-2-fluoro-phenyl)-8-methyl-6,6-dioxo-6λ6-thia-9-aza-spiro[4.5]dec-2-en-10-thione (300 mg, 742 μmol, Eq: 1.00) and ammonia (7 N in MeOH) (7.87 g, 10 ml, 70.0 mmol, Eq: 94.3) was stirred in a sealed tube for 48 hours at 60° C. Extracted with ethyl acetate and sat. NaHCO3-sol., dried the organic layer over Na2SO4, filtered and evaporated. The residue was chromatographed with ethyl acetate to give (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 (249 mg, 643 μmol, 86.7% yield) as a white foam. MS (ISP): m/z=387.3 [M+H]+ and 389.3 [M+2+H]+.

Workup

  1. extractionExtracted with ethyl acetate and sat. NaHCO3-sol
  2. dry with material, dried the organic layer over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was chromatographed with ethyl acetate

Sources & evidence

ORD record
ord-0014c4eb97a94eb292b39a155d2118b0
Source dataset
uspto-grants-2016_03
Patent number
US09273042B2

Reaction notes

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