N,N,N',N'-Tetramethylmethanediamine → Umifenovir

HRID 1614702Notes

Reaction equation

HRID 1614702 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:7]([CH2:12][S:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:8]2[CH3:11])=[CH:4][C:3]=1[OH:25].[CH3:26][N:27]([CH2:29]N(C)C)[CH3:28]>O>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:7]([CH2:12][S:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:8]2[CH3:11])=[C:4]([CH2:26][N:27]([CH3:29])[CH3:28])[C:3]=1[OH:25]

Participants

4

Reactant 2

HCID 5829N,N,N',N'-TetramethylmethanediamineHCID 1252264SI 5 (pharmaceutical)

Product 1

HCID 131411UmifenovirYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution containing ethyl 6-bromo-5-hydroxy-1-methyl-2-phenylthiomethylindole-3-carboxylate (76.4 g, 0.18 mole) in 470 ml of diowane was added bis-dimethylaminomethane (50 ml, 0.36 mole). The reaction mixture was refluxed for 3 hours, cooled, diluted with a 3-4-fold amount of water. The precipitated crystalls were removed, washed with water and dried to give 60.1 g (70%) of ethyl 6-bromo-5-hydroxy-4-dimethylaminomethyl-1-methyl-2-phenylthiomethylindole-3-carboxilate; m.p. 125°-126° C.

Workup

  1. temperatureThe reaction mixture was refluxed for 3 hours
  2. temperaturecooled
  3. customThe precipitated crystalls were removed
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-5779a249b6ec4dfd90930be2eb3df232
Source dataset
uspto-grants-1993_03
Patent number
US05198552

Reaction notes

Loading…