Pyridine → HCID 68891743, compound

HRID 2220222Notes

Reaction equation

HRID 2220222 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.[N:25]1([S:31](Cl)(=[O:33])=[O:32])[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>ClC(Cl)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:12][N:11]([S:31]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)(=[O:33])=[O:32])[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 12798265Morpholine-4-sulfonyl chlorideHCID 68893382HCID 68893382, compound

Product 1

HCID 68891743HCID 68891743, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
100 °C

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 morpholine-4-sulfonyl chloride (22 mg, 0.12 mmol). The reaction mixture was stirred at 100° C. for four hours then concentrated, diluted with MeOH and filtered. The crude product was purified by preparative reversed-phase HPLC to afford Example 338A (32 mg). HPLC Rt=3.89 min. m/z=469 (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-a78e161acb7444cf840432e63cd8616a
Source dataset
uspto-grants-2008_08
Patent number
US07417040B2

Reaction notes

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