Dimethyl N-cyanodithioiminocarbonate → HCID 178503908, compound

HRID 2037471Notes

Reaction equation

HRID 2037471 reaction equation
[NH2:1][CH2:2][CH2:3][C@@:4]1([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[F:26])=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1.[C:34]([N:36]=[C:37](SC)[S:38][CH3:39])#[N:35]>C(#N)C>[C:34]([N:36]=[C:37]([S:38][CH3:39])[NH:1][CH2:2][CH2:3][C@@:4]1([C:27]2[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:14]=[CH:15][C:16]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[F:26])=[CH:17][CH:18]=2)[CH3:12])[CH2:6][CH2:5]1)#[N:35]

Participants

4

Reactant 2

HCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 53473235HCID 53473235, compound

Product 1

HCID 178503908HCID 178503908, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of (R)-6-(2-aminoethyl)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluoro phenyl)-1,3-oxazinan-2-one (40 mg, 0.09 mmol) and dimethyl cyanocarbonimidodithioate (40 mg, 0.27 mmol) in acetonitrile (4 mL) was heated to reflux overnight. The solvent was removed to give methyl N′-cyano-N-(2-((R)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)ethyl)carbamimidothioate (50 mg, crude), which was used for the next step without purification.

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customThe solvent was removed

Sources & evidence

ORD record
ord-e3696ed98c264189a98f06dce5eed6f0
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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