Pyridine → HCID 22185367, compound

HRID 1795144Notes

Reaction equation

HRID 1795144 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:19]([CH3:23])([CH3:22])[CH2:20][NH2:21])[NH:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:4][C:3]=1[O:24][CH3:25].N1C=CC=CC=1.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>ClCCl.C(=O)([O-])O.[Na+]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:19]([CH3:23])([CH3:22])[CH2:20][NH:21][S:33]([CH3:32])(=[O:35])=[O:34])[NH:11][C:12]=2[C:13]2[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=2)=[CH:4][C:3]=1[O:24][CH3:25]

Participants

6

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 22185381HCID 22185381, compound

Product 1

HCID 22185367HCID 22185367, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of Example 2 (178 mg, 0.5 mmol) in dichloromethane (10 ml) containing pyridine (0.12 ml, 1.5 mmol) at 0° C. was treated with a solution of methanesulfonyl chloride (57.3 mg, 0.5 mmol) in dichloromethane (1 ml). The solution was stirred at 0° C. for 1 hour followed by 30 min at room temperature before being diluted with dichloromethane and saturated sodium hydrogen carbonate solution. The aqueous layer was then separated and extracted with additional dichloromethane. The combined organic extracts were washed with brine, dried over anhydrous magnesium sulphate, filtered and concentrated at reduced pressure. The residue was chromatographed on silica gel eluting with dichloromethane/methanol/0.880 ammonia solution (8:1:0.1) to give the title compound (85 mg, 40%) as a pale yellow solid; MS(ES+) m/e 435/437 [M+H]+.

Workup

  1. waitfollowed by 30 min at room temperature
  2. customThe aqueous layer was then separated
  3. extractionextracted with additional dichloromethane
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over anhydrous magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated at reduced pressure
  8. customThe residue was chromatographed on silica gel eluting with dichloromethane/methanol/0.880 ammonia solution (8:1:0.1)

Sources & evidence

ORD record
ord-735b244cfafa47ef90578d7d5175821c
Source dataset
uspto-grants-2006_04
Patent number
US07026336B1

Reaction notes

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