2-Chlorobenzenesulfonyl chloride → HCID 86686905, compound

HRID 2363852Notes

Reaction equation

HRID 2363852 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.[Cl:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[S:31](Cl)(=[O:33])=[O:32].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:31]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[Cl:24])(=[O:33])=[O:32])[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 761872-Chlorobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 86686890HCID 86686890, compound

Product 1

HCID 86686905HCID 86686905, compoundYield 66%

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; 108 mg, 0.34 mmol) and 2-chlorobenzenesulfonyl chloride (145 mg, 0.69 mmol) in THF (6 mL) was added excess N,N-diisopropylethylamine (179 μL, 1.0 mmol) at 0° C. under a nitrogen atmosphere. The resulting light brown solution was allowed to warm slowly to room temperature over 2 hours, was and then stirred for 15 hours at room temperature under a nitrogen atmosphere. The reaction mixture was diluted with water and brine solution and the organic compound was extracted with ethyl acetate (2×50 mL). The combined extracts were washed with brine solution and dried over anhydrous magnesium sulfate. Filtration and concentration gave a crude brown oil which was purified by flash chromatography (40 g ISCO column, eluting with 0-60% ethyl acetate/hexanes) to give {4-[1-(2-chloro-benzenesulfonyl)-piperidin-4-yl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid methyl ester (110 mg, 65%) as an off-white solid. MS cald. for C25H26ClFNO4S [(M+H)+] 490, obsd. 490.0.

Workup

  1. extractionthe organic compound was extracted with ethyl acetate (2×50 mL)
  2. washThe combined extracts were washed with brine solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationFiltration and concentration
  5. customgave a crude brown oil which
  6. customwas purified by flash chromatography (40 g ISCO column, eluting with 0-60% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-b41ab20299084ed6bb5296a66a44ae3c
Source dataset
uspto-grants-2014_04
Patent number
US08691993B2

Reaction notes

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