Ethanolamine → HCID 178432315, compound

HRID 1085137Notes

Reaction equation

HRID 1085137 reaction equation
[Cl:1][C:2]1[C:29]([Cl:30])=[CH:28][C:5]2[NH:6][C:7](=S)[CH2:8][C:9]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[C:25]5[CH:24]=[CH:23][N:22]=[CH:21][C:20]=5[N:19]=[C:18]4[CH3:26])=[CH:13][CH:12]=3)=[N:10][C:4]=2[CH:3]=1.[CH2:31]([CH2:33][NH2:34])[OH:32]>C(O)CCC.C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:29]([Cl:30])=[CH:28][C:5]2[N:6]=[C:7]([NH:34][CH2:33][CH2:31][OH:32])[CH2:8][C:9]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[C:25]5[CH:24]=[CH:23][N:22]=[CH:21][C:20]=5[N:19]=[C:18]4[CH3:26])=[CH:13][CH:12]=3)=[N:10][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 700EthanolamineHCID 10479006HCID 10479006, compound

Product 1

HCID 178432315HCID 178432315, compound

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 1140TolueneSolvent

Procedure

A mixture of 7,8-dichloro-2,3-dihydro-4-[4-(2-methylimidazo[4,5-c]pyrid-1-yl)phenyl]-1H-[1,5]benzodiazepin-2-thione (453 mg, 1.0 mmol), ethanolamine (122 mg, 2.0 mmol) and red mercuric oxide (216 mg, 1.0 mmol) was heated in n-butanol (5 ml) at reflux for 1 hour. The mixture was cooled, diluted with an equal volume of toluene and filtered through Arbocel filter aid. The filtrate was concentrated under reduced pressure, and the residue was purified by flash chromatography, eluting with ethyl acetate:methanol=4:1. Fractions containing product were evaporated yielding 7,8-dichloro-2-[2-hydroxyethylamino]-4-[4-(2-methylimidazo[4,5-c]pyrid-1-yl)phenyl]-3H-[1,5]-benzodiazepine as a yellow foam, (345 mg, 72%).

Workup

  1. temperatureat reflux for 1 hour
  2. temperatureThe mixture was cooled
  3. filtrationfiltered through Arbocel
  4. filtrationfilter aid
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by flash chromatography
  7. washeluting with ethyl acetate
  8. additionFractions containing product
  9. customwere evaporated

Sources & evidence

ORD record
ord-5a39bf8284d045218070239cedd82ba4
Source dataset
uspto-grants-1991_04
Patent number
US05008263

Reaction notes

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