Pyridine → HCID 58020013, compound

HRID 1632116Notes

Reaction equation

HRID 1632116 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[C:10]([CH2:16][C:17]3[CH:18]=[C:19]([NH2:23])[CH:20]=[CH:21][CH:22]=3)[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>O>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[C:10]([CH2:16][C:17]3[CH:18]=[C:19]([NH:23][S:31]([CH3:30])(=[O:33])=[O:32])[CH:20]=[CH:21][CH:22]=3)[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 58020122HCID 58020122, compound

Product 1

HCID 58020013HCID 58020013, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 4 mL vial was added P-255 (60 mg, 0.17 mmol), followed by pyridine (2 mL) then methanesulfonyl chloride (13 μL) at 0° C. The resulting solution was allowed to stir at room temperature overnight. The reaction mixture was diluted with water (10 mL) and extracted with ethyl acetate (3×5 mL). The combined organics were concentrated under vacuum, and the residue was purified by silica gel column chromatography with methanol/dichloromethane to yield 36.7 mg (55%) of P-271). 1H NMR (400 MHz, CDCl3) 2.98 (s, 3H), 3.79 (s, 3H), 3.94 (s, 2H), 6.53 (s, 1H), 6.91 (d, J=8.4 Hz, 1H), 6.99-7.17 (m, 5H), 7.22-7.35 (m, 3H), 7.34-7.41 (m, 1H), 7.48 (s, 1H) ppm.

Workup

  1. customat 0° C
  2. extractionextracted with ethyl acetate (3×5 mL)
  3. concentrationThe combined organics were concentrated under vacuum
  4. customthe residue was purified by silica gel column chromatography with methanol/dichloromethane

Sources & evidence

ORD record
ord-c367209e4e1542588e43612588639c88
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

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