Benzylamine → 10-[[6-[(Phenylmethyl)amino]-3-pyridinyl]carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine

HRID 1940805Notes

Reaction equation

HRID 1940805 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[CH2:14][N:13]3[CH:21]=[CH:22][CH:23]=[C:12]3[CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[CH2:24]([NH2:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN1C(=O)N(C)CCC1>[C:25]1([CH2:24][NH:31][C:2]2[N:7]=[CH:6][C:5]([C:8]([N:10]3[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=4[CH2:14][N:13]4[CH:21]=[CH:22][CH:23]=[C:12]4[CH2:11]3)=[O:9])=[CH:4][CH:3]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 2194772510-[(6-Chloro-3-pyridinyl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine

Product 1

HCID 1891750410-[[6-[(Phenylmethyl)amino]-3-pyridinyl]carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine

Reagents, catalysts & solvents 1

HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Conditions

Temperature
110 °C

Procedure

A mixture of 0.16 g of 10-[(6-chloro-3-pyridinyl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine, 0.5 ml of benzylamine and 0.2 ml of N,N'-dimethylpropyleneurea is stirred and heated at 110° C. for 7 hours. After cooling to room temperature, the mixture is washed with hexane (3 times 10 ml). The residue is dissolved in water and made alkaline with 1N NaOH. The suspension is washed with H2O and extracted with ethyl acetate. The organic extract is washed with brine, dried (Na2SO4) and filtered through a thin pad of hydrous magnesium silicate. The filtrate is evaporated and the residue triturated with diethyl ether-hexane to give 0.20 g of white solid; mass spectrum (CI) 395 (M+H).

Workup

  1. temperatureAfter cooling to room temperature
  2. washthe mixture is washed with hexane (3 times 10 ml)
  3. dissolutionThe residue is dissolved in water
  4. washThe suspension is washed with H2O
  5. extractionextracted with ethyl acetate
  6. extractionThe organic extract
  7. washis washed with brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered through a thin pad of hydrous magnesium silicate
  10. customThe filtrate is evaporated
  11. customthe residue triturated with diethyl ether-hexane

Sources & evidence

ORD record
ord-6a4028aec77d4b0db144e41f25e51916
Source dataset
uspto-grants-1997_12
Patent number
US05700796

Reaction notes

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