Dimethyl N-cyanodithioiminocarbonate → HCID 178504233, compound

HRID 340562Notes

Reaction equation

HRID 340562 reaction equation
[NH2:1][CH2:2][CH:3]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([C:15]2[N:16]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[CH:17]=[C:18]([C:20]#[N:21])[N:19]=2)=[O:14])=[C:8]([C:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]=2)[CH:7]=1)[CH2:4][NH2:5].CS[C:38](SC)=[N:39][C:40]#[N:41]>C(Cl)Cl>[C:40]([N:39]=[C:38]1[NH:1][CH2:2][CH:3]([C:6]2[CH:11]=[CH:10][C:9]([NH:12][C:13]([C:15]3[N:16]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:27])[CH3:28])[CH:17]=[C:18]([C:20]#[N:21])[N:19]=3)=[O:14])=[C:8]([C:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]=3)[CH:7]=2)[CH2:4][NH:5]1)#[N:41]

Participants

4

Reactant 2

HCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 597712334-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [4-(2-amino-1-aminomethyl-ethyl)-2-cyclohex-1-enyl-phenyl]-amide

Product 1

HCID 178504233HCID 178504233, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [4-(2-amino-1-aminomethyl-ethyl)-2-cyclohex-1-enyl-phenyl]-amide (as prepared in the previous step, 15 mg, 0.030 mmol) in DCM (10 mL), dimethyl N-cyanodithioiminocarbonate (4.2 mg, 0.28 mmol) was added. The resulting solution was heated at reflux for 4 h. The reaction mixture was allowed to cool to RT and was concentrated in vacuo. The residue obtained was purified on silica (20-100% EtOAc-hexane) to obtain the title compound (11 mg, 62%): Mass spectrum (ESI, m/z): Calcd. for C28H36N8O2Si, 545.3 (M+H). found 545.1.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for 4 h
  3. concentrationwas concentrated in vacuo
  4. customThe residue obtained
  5. customwas purified on silica (20-100% EtOAc-hexane)

Sources & evidence

ORD record
ord-88f17a739acd46e8910a05dece33e879
Source dataset
uspto-grants-2014_11
Patent number
US08895584B2

Reaction notes

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