Methanesulfonyl chloride → HCID 86686906, compound

HRID 2363854Notes

Reaction equation

HRID 2363854 reaction equation
[CH3:1][O:2][C:3](=[O:23])[CH2:4][C:5]1[C:14]([CH3:15])=[C:13]([CH:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:22])[CH:11]=2)[CH:6]=1.[CH3:24][S:25](Cl)(=[O:27])=[O:26].C(N(CC)C(C)C)(C)C>C1COCC1.O.[Cl-].[Na+].O>[CH3:1][O:2][C:3](=[O:23])[CH2:4][C:5]1[C:14]([CH3:15])=[C:13]([CH:16]2[CH2:17][CH2:18][N:19]([S:25]([CH3:24])(=[O:27])=[O:26])[CH2:20][CH2:21]2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:22])[CH:11]=2)[CH:6]=1

Participants

7

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 86686890HCID 86686890, compound

Product 1

HCID 86686906HCID 86686906, compoundYield 55%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of (6-fluoro-3-methyl-4-piperidin-4-yl-naphthalen-2-yl)-acetic acid methyl ester (which may be prepared as described above; 82 mg, 0.26 mmol) and methanesulfonyl chloride (59.6 mg, 0.52 mmol) in THF (6.0 mL) was added N,N-diisopropylethylamine (227 μL, 1.3 mmol) at 0° C. under a nitrogen atmosphere. The resulting suspension was allowed to warm to room temperature during a period of 2 hours and then stirred for 15 hours under a nitrogen atmosphere. The reaction mixture was diluted with water and brine solution, and the organic compound was extracted with ethyl acetate (2×75 mL). The combined organic extracts were washed with brine solution and dried over anhydrous MgSO4, filtered, and concentrated to give a crude brown oil which was purified by flash chromatography (40 g ISCO column, eluting with 0-100% ethyl acetate/hexanes) to give [6-fluoro-4-(1-methanesulfonyl-piperidin-4-yl)-3-methyl-naphthalen-2-yl]-acetic acid methyl ester (56 mg, 55%) as an off-white solid. MS cald. for C20H25FNO4S [(M+H)+] 394, obsd. 393.9.

Workup

  1. extractionthe organic compound was extracted with ethyl acetate (2×75 mL)
  2. washThe combined organic extracts were washed with brine solution
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude brown oil which
  7. customwas purified by flash chromatography (40 g ISCO column, eluting with 0-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-a92408246d09425b82b7ff297ed3ff9c
Source dataset
uspto-grants-2014_04
Patent number
US08691993B2

Reaction notes

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