Triethylamine → HCID 54214821, compound

HRID 1646191Notes

Reaction equation

HRID 1646191 reaction equation
Cl[C:2]([N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:8](=[O:15])[NH:7][C:6]2[CH:16]=[CH:17][CH:18]=[N:19][C:5]1=2)=[O:3].[CH3:20][N:21]1[CH2:30][CH2:29][CH:28]2[CH:23]([CH2:24][CH2:25][CH2:26][NH:27]2)[CH2:22]1.C(N(CC)CC)C>O1CCCC1>[CH3:20][N:21]1[CH2:30][CH2:29][C@@H:28]2[C@H:23]([CH2:24][CH2:25][CH2:26][N:27]2[C:2]([N:4]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[C:8](=[O:15])[NH:7][C:6]3[CH:16]=[CH:17][CH:18]=[N:19][C:5]2=3)=[O:3])[CH2:22]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1104396211-chlorocarbonyl-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-oneHCID 15106928135037-28-4

Product 1

HCID 54214821HCID 54214821, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.64 g (5.0 mmoles) of 11-(chlorocarbonyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one, 0.8 g (5.2 mmoles) of 8-methyl-2,8-diazabicyclo[4.4.0]decane and 0.85 ml (6.0 mmoles) of triethylamine in 20 ml of tetrahydrofuran was stirred for 3 hours at ambient temperature. The reaction mixture was concentrated in vacuo and the residue was divided between ethyl acetate and dilute aqueous potassium carbonate solution. The organic phase was separated off, dried and concentrated in vacuo. Chromatographic purification took place on silica gel (30-60 μm) using the solvent mixture ethyl acetate/methanol/concentrated ammonia 70/30/1, v/v/v. The two main fractions were concentrated, ground with acetonitrile and the resulting precipitate was filtered off. 100 mg (5% of theory) of crystals of m.p. 230°-233° C., which were identified as trans compound using spectroscopic methods, were obtained from the main fraction eluted initially. The subsequent main fraction contained 200 mg (10% of theory) of the crystalline cis compound of m.p. 160°-161° C.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe organic phase was separated off
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customChromatographic purification
  6. concentrationThe two main fractions were concentrated
  7. filtrationground with acetonitrile and the resulting precipitate was filtered off
  8. customwere obtained from the main fraction
  9. washeluted initially

Sources & evidence

ORD record
ord-deb3aa27726d464e8fcfa463d2c4c1e6
Source dataset
uspto-grants-1993_01
Patent number
US05179090

Reaction notes

Loading…