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

HRID 1290949Notes

Reaction equation

HRID 1290949 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.[CH3:24][CH:25]([CH3:28])[CH2:26][NH2:27].CC1N(C(N(C)C)=O)C1>N1C=CC=CC=1>[CH3:24][CH:25]([CH3:28])[CH2:26][NH:27][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

Participants

5

Reactant 3

HCID 6558IsobutylamineHCID 11007919N,N,2-trimethylaziridine-1-carboxamideHCID 2194772510-[(6-Chloro-3-pyridinyl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine

Product 1

HCID 1891756210-[[6-[(2-Methylpropyl)amino]-3-pyridinyl]carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °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, 40 mg of pyridine and 2 ml of 2-methylpropylamine is stirred and heated at 100° C. in a sealed vessel for 1 hour. To the mixture is added 0.2 ml of N,N-dimethylpropyleneurea and the mixture is heated at 110° C. for 7 hours. The volatiles are removed under vacuum and 10 ml of 0.5N NaOH is added to the residue. The mixture is filtered and the solid washed with water and then hexane. The solid is dissolved in ethyl acetate and the solution washed with 0.5N NaOH, brine and dried (Na2 SO4). The solution is filtered through a thin pad of hydrous magnesium silicate and the filtrate concentrated to dryness. The residue is triturated with diisopropylether-hexane to give 0.18 g of white solid; mass spectrum (CI) 361 (M+H).

Workup

  1. temperaturethe mixture is heated at 110° C. for 7 hours
  2. customThe volatiles are removed under vacuum and 10 ml of 0.5N NaOH
  3. additionis added to the residue
  4. filtrationThe mixture is filtered
  5. washthe solid washed with water
  6. dissolutionThe solid is dissolved in ethyl acetate
  7. washthe solution washed with 0.5N NaOH, brine
  8. customdried (Na2 SO4)
  9. filtrationThe solution is filtered through a thin pad of hydrous magnesium silicate
  10. concentrationthe filtrate concentrated to dryness
  11. customThe residue is triturated with diisopropylether-hexane

Sources & evidence

ORD record
ord-3ac4ff9caa6f4702a44c849a629ea0b0
Source dataset
uspto-grants-1998_05
Patent number
US05753648

Reaction notes

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