Ammonia → HCID 86715829, compound

HRID 920174Notes

Reaction equation

HRID 920174 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:21])=[C:6]([C@@:8]2([CH3:20])[NH:16][C:15](=S)[C:11]3([CH2:14][CH2:13][CH2:12]3)[S:10](=[O:19])(=[O:18])[CH2:9]2)[CH:7]=1.[NH3:22]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:21])=[C:6]([C@@:8]2([CH3:20])[N:16]=[C:15]([NH2:22])[C:11]3([CH2:14][CH2:13][CH2:12]3)[S:10](=[O:19])(=[O:18])[CH2:9]2)[CH:7]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 90025425HCID 90025425, compound

Product 1

HCID 86715829HCID 86715829, compoundYield 55.8%

Conditions

Temperature
60 °C

Procedure

A mixture of (R)-7-(5-bromo-2-fluoro-phenyl)-7-methyl-5,5-dioxo-5λ6-thia-8-aza-spiro[3.5]nonan-9-thione (1.05 g, 2.68 mmol, Eq: 1.00) and ammonia (7 N in MeOH) (19.1 ml, 134 mmol, Eq: 50) was stirred in a sealed tube for 40 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 on 20 g silica gel with ethyl acetate to give (R)-7-(5-bromo-2-fluoro-phenyl)-7-methyl-5,5-dioxo-5λ6-thia-8-aza-spiro[3.5]non-8-en-9-ylamine (560 mg, 1.49 mmol, 55.8% yield) as a white solid. MS (ISP): m/z=375.0 [M+H]+ and 377.4 [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 on 20 g silica gel with ethyl acetate

Sources & evidence

ORD record
ord-1c9a9178e7fa4fea8241952b489f028b
Source dataset
uspto-grants-2016_03
Patent number
US09273042B2

Reaction notes

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