N-[bis(methylsulfanyl)methylidene]methanesulfonamide → HCID 178504234, compound

HRID 408931Notes

Reaction equation

HRID 408931 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][S:40]([CH3:43])(=[O:42])=[O:41]>ClCCCl>[C:30]1([C:8]2[CH:7]=[C:6]([CH:3]3[CH2:2][NH:1][C:38](=[N:39][S:40]([CH3:43])(=[O:42])=[O:41])[NH:5][CH2:4]3)[CH:11]=[CH:10][C:9]=2[NH:12][C:13]([C:15]2[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]=2)=[O:14])[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]=1

Participants

4

Reactant 2

HCID 13449843N-[bis(methylsulfanyl)methylidene]methanesulfonamideHCID 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 178504234HCID 178504234, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

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 Example 12, step (d), 250 mg, 0.506 mmol) and N-(bis-methylsulfanyl-methylene)-methanesulfonamide (Australian Journal of Chemistry, 46(6), 873, (1993), 100 mg, 0.506 mmol) in 1,2-dichloroethane (20 mL) was heated at reflux for 4 h. The reaction mixture was concentrated, and the residue was purified on silica (20-100% EtOAc-hexane) to obtain the title compound (117 mg, 39%): Mass spectrum, (ESI, m/z): Calcd. for C28H39N7O4SSi, 598.2 (M+H). found 598.2.

Workup

  1. temperatureat reflux for 4 h
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified on silica (20-100% EtOAc-hexane)

Sources & evidence

ORD record
ord-d43abc8076934c0dbafda3da33ceca85
Source dataset
uspto-grants-2014_06
Patent number
US08759347B2

Reaction notes

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