Pyridine → HCID 69196441, compound

HRID 2220220Notes

Reaction equation

HRID 2220220 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:12][NH:11][C:10]3[CH:13]=[CH:14][C:15]([Cl:17])=[CH:16][C:9]=3[CH:8]=[CH:7][C:6]=2[CH:18]=1.N1C=CC=CC=1.[CH:25]1([C:28](Cl)=[O:29])[CH2:27][CH2:26]1>ClC(Cl)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:12][N:11]([C:28]([CH:25]3[CH2:27][CH2:26]3)=[O:29])[C:10]3[CH:13]=[CH:14][C:15]([Cl:17])=[CH:16][C:9]=3[CH:8]=[CH:7][C:6]=2[CH:18]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 77637Cyclopropanecarbonyl chlorideHCID 68893382HCID 68893382, compound

Product 1

HCID 69196441HCID 69196441, compoundYield 85.8%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A solution of 9-Bromo-2-chloro-5,6-dihydro-dibenzo[b,f]azocine (30 mg, 0.09 mmol) (prepared in a manner analogous to that described for Example 1F) in dichloroethane was treated with pyridine (0.02 mL, 0.27 mmol) and cyclopropanecarbonyl chloride (0.011 mL, 0.12 mmol). The reaction mixture was stirred at room temperature for two hours then concentrated, diluted with MeOH and filtered. The crude product was purified by preparative reversed-phase HPLC to afford Example 326A (30 mg, 82%). HPLC Rt=4.05 min. m/z=388 (M+H+)

Workup

  1. concentrationthen concentrated
  2. additiondiluted with MeOH
  3. filtrationfiltered
  4. customThe crude product was purified by preparative reversed-phase HPLC

Sources & evidence

ORD record
ord-5b86ed301a7341349af4570d5f6acd8f
Source dataset
uspto-grants-2008_08
Patent number
US07417040B2

Reaction notes

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