Aminoacetaldehyde dimethyl acetal → HCID 136395936, compound

HRID 1489522Notes

Reaction equation

HRID 1489522 reaction equation
[C:1]1([C:7]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[NH:11][C:10](=S)[CH:9]([NH:19][C:20](=[O:31])[CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=3[Cl:30])[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:32][O:33][CH:34]([O:37][CH3:38])[CH2:35][NH2:36]>C1COCC1>[CH3:32][O:33][CH:34]([O:37][CH3:38])[CH2:35][N:36]=[C:10]1[CH:9]([NH:19][C:20](=[O:31])[CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=2[Cl:30])[N:8]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[NH:11]1

Participants

4

Reactant 2

HCID 89728Aminoacetaldehyde dimethyl acetalHCID 22902085HCID 22902085, compound

Product 1

HCID 136395936HCID 136395936, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N-(2,3-dihydro-5-phenyl-2-thioxo-1H-1,4-benzodiazepin-3-yl)-3-(2,4-dichlorophenyl)propanamide (234 mg, 0.5 mmol) and 2,2-dimethoxyethylamine (210 mg, 2 mmol) in THF (6 mL) was stirred at room temperature for 17 h. Mercuric chloride (0.20 g, 0.75 mmol) was added and the mixture was stirred at 55° C. for 3 h. The solvent was evaporated under reduced pressure and the residue was dissolved in ethyl acetate (20 mL). The mixture was washed with aqueous citric acid (10%, 5 mL), brine (5 mL), saturated aqueous sodium carbonate (5 mL) and brine (5 mL), dried (Na2 SO4) and the solvent was evaporated under reduced pressure to give N-[2,3-dihydro-2-(2,2-dimethoxyethylimino)-5-phenyl-1H-1,4-benzodiazepin-3-yl)-3-(2,4-dichlorophenyl)propanamide as a solid. The residue was dissolved in aqueous sulfuric acid (50%, 1 mL) and mercuric chloride (0.20 g, 0.75 mmol) was added. The mixture was stirred at room temperature for 18 h., cooled to 0° C. and the pH was adjusted to 7.0 with aqueous sodium hydroxide (10%). The mixture was extracted with ethyl acetate and the combined organic fractions were washed with water and brine, dried (Na2SO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with CH2Cl2 /MeOH (99.5:0.5) to give 3-(2,4-dichlorophenyI)-N-{6-phenyl-4H-imidazo[1,2-a][1,4]benzodiazepin-4-yl}propanamide as a solid, m.p. 183°-184° C.

Workup

  1. stirringthe mixture was stirred at 55° C. for 3 h
  2. customThe solvent was evaporated under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate (20 mL)
  4. washThe mixture was washed with aqueous citric acid (10%, 5 mL), brine (5 mL), saturated aqueous sodium carbonate (5 mL) and brine (5 mL)
  5. customdried (Na2 SO4)
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-839d5a8f69dd4c3393163682ef8f8de4
Source dataset
uspto-grants-1997_10
Patent number
US05679672

Reaction notes

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