Ethyl Acetate → HCID 178428587, compound

HRID 1936580Notes

Reaction equation

HRID 1936580 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:5]2[N:6]=[CH:7][NH:8][C:4]=2[C:3]=1[CH3:12].C([N:15]=[C:16](S)[N:17](C(OCC1C=CC=CC=1)=O)[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])C.[C:39]([O:42][CH2:43][CH3:44])(=[O:41])C>CO>[CH2:43]([O:42][C:39]([N:15]=[C:16]([NH:17][C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])[NH:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:5]2[N:6]=[CH:7][NH:8][C:4]=2[C:3]=1[CH3:12])=[O:41])[C:44]1[CH:9]=[CH:10][CH:2]=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 183798614,7-dimethyl-3H-benzimidazol-5-amineHCID 178465517HCID 178465517, compound

Product 1

HCID 178428587HCID 178428587, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 430 mg of 5-amino-4,7-dimethylbenzimidazole in 100 mL of ethyl acetate and 10 mL of methanol are added 19 of ethyl N,N-bis(benzyloxycarbonyl)pseudothiourea and 855 mg of mercuric acetate and the mixture is stirred at room temperature for 15 hours. The mixture is rotary evaporated and the residue is purified by flash column chromatography on silica gel, eluting with 5% methanol/ethyl acetate to provide 1.01 g of 5-[N2,N3-bis(benzyloxycarbonyl)guanidino]-4,7-dimethybenzimidazole as a glassy solid.

Workup

  1. customThe mixture is rotary evaporated
  2. customthe residue is purified by flash column chromatography on silica gel
  3. washeluting with 5% methanol/ethyl acetate

Sources & evidence

ORD record
ord-6acd38e75d2a45e4926713264d2981e5
Source dataset
uspto-grants-2002_05
Patent number
US06391878B2

Reaction notes

Loading…