4-Pyridinecarboxylic acid, 1-oxide → HCID 131717533, compound

HRID 1886431Notes

Reaction equation

HRID 1886431 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:16](=[C:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[C:10]3=[N:11][CH:12]=[C:13]([CH3:15])[CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:23]=1.[C:24](O)(=[O:32])[C:25]1[CH:30]=[CH:29][N+:28]([O-])=[CH:27][CH:26]=1.[OH:34]N1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:16](=[C:17]3[CH2:22][CH2:21][N+:20]([O-:34])([C:24]([C:25]4[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=4)=[O:32])[CH2:19][CH2:18]3)[C:10]3=[N:11][CH:12]=[C:13]([CH3:15])[CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:23]=1

Participants

6

Reactant 4

HCID 261304-Pyridinecarboxylic acid, 1-oxideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 15780496HCID 15780496, compound

Product 1

HCID 131717533HCID 131717533, compoundYield 56.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 20 g of 8-chloro-11-(4-piperidylidene)-6,11-dihydro-3-methyl-5H-benzo[5,6]cyclohepta[1,2-b]pyridine (product from Preparative Example 7, Step E), 1.39 g of isonicotinic acid N-oxide, and 1.35 g of 1-hydroxybenzotriazole in 60 mL CH2Cl2 at 0° C. was added 1.91 g of 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (DEC). The reaction mixture was slowly allowed to warm to room temperature overnight. The reaction mixture was quenched with water, basified with 10% NaOH, and extracted with CH2Cl2. The combined organic portions were washed with brine, dried over Na2SO4, and concentrated in vacuo. The product was flash chromatographed using 5% methanol in methylene chloride to give 2.52 g of a product which could be triturated with CH2Cl2 /diisopropylether (1:20 parts by volume) to give the title compound as a white solid.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with CH2Cl2
  3. washThe combined organic portions were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customchromatographed

Sources & evidence

ORD record
ord-ae650837f8e442fb8835b7bb06f5b0ce
Source dataset
uspto-grants-1992_09
Patent number
US05151423

Reaction notes

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