Acetonitrile → HCID 54001000, compound

HRID 1681820Notes

Reaction equation

HRID 1681820 reaction equation
Cl[C:2]1[C:6]2[N:7]([C:17](=[O:34])[CH2:18][N:19]3[CH2:24][CH2:23][CH:22]([CH2:25][CH2:26][CH2:27][CH2:28][N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])[CH2:21][CH2:20]3)[C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[NH:10][C:11](=[O:12])[C:5]=2[N:4]([CH3:35])[CH:3]=1.C(#N)C>C(O)=O.CN(C)C=O.[Pd]>[CH2:32]([N:29]([CH2:30][CH3:31])[CH2:28][CH2:27][CH2:26][CH2:25][CH:22]1[CH2:23][CH2:24][N:19]([CH2:18][C:17]([N:7]2[C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[NH:10][C:11](=[O:12])[C:5]3[N:4]([CH3:35])[CH:3]=[CH:2][C:6]2=3)=[O:34])[CH2:20][CH2:21]1)[CH3:33]

Participants

6

Reactant 2

HCID 6342AcetonitrileHCID 19804210HCID 19804210, compound

Product 1

HCID 54001000HCID 54001000, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst2×HCID 284Formic AcidSolvent3×HCID 6228DimethylformamideSolvent

Procedure

4.715 g (9.7 millimol) of 3-chloro-4-[[4-[4-(diethylamino)-butyl]-1-piperidinyl]acetyl ]-1-methyl-1,4,9,10-tetrahydropyr rolo[3,2-b][1,5]benzodiazepin- 10-one were dissolved in a mixture of 5 ml of 85% formic acid and 25 ml of dimethylformamide and after the addition of 0.5 g of 10% palladium/activated charcoal the mixture was refluxed for 3 hours. 7.0 ml of formic acid were added, the mixture was refluxed for a further 6 hours and then, after the addition of a further 4.0 ml of formic acid and 0.8 g of 10% palladium/activated charcoal, the mixture was finally refluxed for a further 8 hours. The mixture was filtered while hot, the filtrate was evaporated down in vacuo and the residue was purified by column chromatography (silica gel; dichloromethane/ethyl acetate/methanol/conc. ammonia 3.5:1.5:0.46:0.06 v/v). 1.45 g (33% of theory) of colourless crystals were obtained, m.p. 196°-198° C. (acetonitrile), which were found according to thin layer chromatography and IR, UV and 1H-NMR spectra, to be identical to a preparation obtained according to Example 39.

Workup

  1. temperaturewas refluxed for 3 hours
  2. temperaturethe mixture was refluxed for a further 6 hours
  3. temperaturethe mixture was finally refluxed for a further 8 hours
  4. filtrationThe mixture was filtered while hot, the filtrate
  5. customwas evaporated down in vacuo
  6. customthe residue was purified by column chromatography (silica gel; dichloromethane/ethyl acetate/methanol/conc. ammonia 3.5:1.5:0.46:0.06 v/v)
  7. custom1.45 g (33% of theory) of colourless crystals were obtained
  8. customobtained

Sources & evidence

ORD record
ord-e044816d5fa44932a98af190ea58577c
Source dataset
uspto-grants-1992_12
Patent number
US05175158

Reaction notes

Loading…