Sodium Hydroxide → HCID 86748759, compound

HRID 1647254Notes

Reaction equation

HRID 1647254 reaction equation
[C:1]([OH:10])(=O)[C:2]1[CH:7]=[CH:6][N+:5]([O-])=[CH:4][CH:3]=1.[Cl:11][C:12]1[CH:32]=[CH:31][C:15]2[CH:16]([N:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)[C:17]3[C:22]([CH2:23][O:24][C:14]=2[CH:13]=1)=[CH:21][CH:20]=[CH:19][N:18]=3.O.[OH:34]N1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[OH-].[Na+]>ClCCl>[Cl:11][C:12]1[CH:32]=[CH:31][C:15]2[CH:16]([N:25]3[CH2:26][CH2:27][N+:28]([O-:34])([C:1]([C:2]4[CH:3]=[CH:4][N:5]=[CH:6][CH:7]=4)=[O:10])[CH2:29][CH2:30]3)[C:17]3[C:22]([CH2:23][O:24][C:14]=2[CH:13]=1)=[CH:21][CH:20]=[CH:19][N:18]=3

Participants

7

Reactant 5

HCID 14798Sodium HydroxideHCID 261304-Pyridinecarboxylic acid, 1-oxideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 15780500HCID 15780500, compound

Product 1

HCID 86748759HCID 86748759, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add isonicotinic acid N-oxide (0.79 g, 5.70 mmole) to 8-chloro-5,11-dihydro-11-(1-piperazinyl)[1]benzoxepino[4,3-b]pyridine (1.50 g, 4.75 mmole) in dichloromethane (30 mL) at 0° C. under a nitrogen atmosphere. Add 1-hydroxybenzotriazole hydrate (0.77 g, 5.70 mmole) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.09 g, 5.70 mmole). Warm the reaction mixture up slowly, and stir for 23 hours at room temperature. Add 1N aqueous sodium hydroxide (50 mL), and separate layers. Extract with dichloromethane (2×50 mL). Wash the organic solution with brine, dry with MgSO4, filter, and concentrate under reduced presure. Dissolve the solid in dichloromethane, and chromatograph on silica gel, eluting with 7% methanol in dichloromethane, then 10% methanol in dichloromethane. Combine the appropriate fractions, and concentrate under reduced pressure to give a light yellow solid. Recrystallize the product from dichloromethane/hexane to obtain the title compound as a white solid (1.97 g, 95% yield): mp 206°-208° C.; MS (CI) m/z 421 [M+ -16].

Workup

  1. temperatureWarm the reaction mixture up slowly, and
  2. customseparate layers
  3. extractionExtract with dichloromethane (2×50 mL)
  4. washWash the organic solution with brine
  5. dry with materialdry with MgSO4
  6. filtrationfilter
  7. concentrationconcentrate under reduced presure
  8. dissolutionDissolve the solid in dichloromethane
  9. washchromatograph on silica gel, eluting with 7% methanol in dichloromethane
  10. concentrationconcentrate under reduced pressure
  11. customto give a light yellow solid
  12. customRecrystallize the product from dichloromethane/hexane

Sources & evidence

ORD record
ord-93ad1d709d374712b809dfebf2d215c6
Source dataset
uspto-grants-1995_07
Patent number
US05430032

Reaction notes

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