Pyridine → HCID 66674320, compound

HRID 423185Notes

Reaction equation

HRID 423185 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[F:6][C:7]1[CH:8]=[CH:9][C:10]2[C:16](=[C:17]([C:20]3[CH:21]=[C:22]([NH2:26])[CH:23]=[CH:24][CH:25]=3)[CH2:18][CH3:19])[C:15]3[CH:27]=[CH:28][CH:29]=[N:30][C:14]=3[CH2:13][O:12][C:11]=2[CH:31]=1.N1C=CC=CC=1.C(=O)(O)[O-].[Na+]>ClCCl>[F:6][C:7]1[CH:8]=[CH:9][C:10]2[C:16](=[C:17]([C:20]3[CH:21]=[C:22]([NH:26][S:2]([CH3:1])(=[O:4])=[O:3])[CH:23]=[CH:24][CH:25]=3)[CH2:18][CH3:19])[C:15]3[CH:27]=[CH:28][CH:29]=[N:30][C:14]=3[CH2:13][O:12][C:11]=2[CH:31]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 66674430HCID 66674430, compound

Product 1

HCID 66674320HCID 66674320, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (0.34 mL, 4.36 mmol) is added dropwise to a solution of 3-[1-(8-fluoro-11H-10-oxa-1-aza-dibenzo[a,d]cyclohepten-5-ylidene)-propyl]-phenylamine (1.37 g, 3.96 mmol) and pyridine (0.35 mL, 4.36 mmol) in dichloromethane (10 mL) at 0° C. After 2 h, 7% aqueous sodium bicarbonate (20 mL) is added and the mixture stirred for 30 min, decanted, and the layers separated. The aqueous phase is washed with dichloromethane (2×20 mL). The organic phases are collected and washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to obtain 1.98 g of crude product. The material is purified by flash chromatography, using Biotage® and eluting with hexane:ethanol (9:1) to afford 1.35 g (80%) of the title compound. LCMS m/e 425 [M−H]+.

Workup

  1. customdecanted
  2. customthe layers separated
  3. washThe aqueous phase is washed with dichloromethane (2×20 mL)
  4. customThe organic phases are collected
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto obtain 1.98 g of crude product
  10. customThe material is purified by flash chromatography
  11. washeluting with hexane:ethanol (9:1)

Sources & evidence

ORD record
ord-943de181730d4ad6bda40164fd1cb734
Source dataset
uspto-grants-2012_01
Patent number
US08101761B2

Reaction notes

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