Pyridine → HCID 69524564, compound

HRID 1373360Notes

Reaction equation

HRID 1373360 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][CH:5]([CH3:25])[CH:6]([S:15]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)(=[O:17])=[O:16])[C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[F:14].N1C=CC=CC=1.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>ClCCl>[Cl:24][C:21]1[CH:20]=[CH:19][C:18]([S:15]([CH:6]([C:7]2[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=2[F:14])[CH:5]([CH3:25])[CH2:4][CH2:3][N:2]([CH3:1])[S:33]([CH3:32])(=[O:35])=[O:34])(=[O:17])=[O:16])=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 69525013HCID 69525013, compound

Product 1

HCID 69524564HCID 69524564, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the amine from Step (b) (0.116 g, 0.3 mmol) in dry dichloromethane (5 ml) was added pyridine (0.060 ml, 0.75 mmol), followed by methanesulfonyl chloride (0.035 ml, 0.45 mmol), and the mixture was stirred at room temperature for 48 hours. After dilution with water (20 ml) and extraction with ethyl acetate (3×20 ml), the combined organic fractions were washed with brine, dried (MgSO4 and evaporated under reduced pressure. The residue was purified by flash chromatography eluting with 10% to 30% ethyl acetate in iso-hexane to give as a mixture of diastereoisomers the title compound as a colourless oil (35 mg, 25%).

Workup

  1. extractionAfter dilution with water (20 ml) and extraction with ethyl acetate (3×20 ml)
  2. washthe combined organic fractions were washed with brine
  3. dry with materialdried (MgSO4
  4. customevaporated under reduced pressure
  5. customThe residue was purified by flash chromatography
  6. washeluting with 10% to 30% ethyl acetate in iso-hexane

Sources & evidence

ORD record
ord-31261fc2bba44c34bd92ac7f7de3b40c
Source dataset
uspto-grants-2007_01
Patent number
US07161006B2

Reaction notes

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