Acetonitrile → HCID 136388339, compound

HRID 1861943Notes

Reaction equation

HRID 1861943 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][C:9]1[CH:14]=[C:13]([NH2:15])[CH:12]=[CH:11][C:10]=1[O:16][CH3:17])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.CS[C:28](=[NH:33])[NH:29][N+:30]([O-:32])=[O:31].C(#N)C>CO>[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][C:9]1[CH:14]=[C:13]([NH:15][C:28]([NH2:33])=[N:29][N+:30]([O-:32])=[O:31])[CH:12]=[CH:11][C:10]=1[O:16][CH3:17])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 22981333tert-Butyl [(5-amino-2-methoxyphenyl)methyl]carbamateHCID 135927615N-Nitro-S-methylisothiourea

Product 1

HCID 136388339HCID 136388339, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of the compound (130 mg) obtained in Example 119, triethylamine (0.09 ml), S-methyl-N-nitroisothiourea (84 mg), acetonitrile (3 ml) and methanol (1 ml) was heated under reflux for 20 h. The reaction mixture was distilled under reduced pressure and the residue was purified by silica gel column chromatography (eluent, chloroform:ethyl acetate=1:1) to give 57.2 mg of the titled compound (yield, 33%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 20 h
  3. distillationThe reaction mixture was distilled under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (eluent, chloroform:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-328f610d947645a4a0b69322f0c8c1e6
Source dataset
uspto-grants-2003_03
Patent number
US06534546B1

Reaction notes

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