Diisopropylethylamine → HCID 86686907, compound

HRID 2363856Notes

Reaction equation

HRID 2363856 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]=[C:29]([Cl:31])[CH:28]=[CH:27][C:26]=1[S:32](Cl)(=[O:34])=[O:33].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:32]([C:26]3[CH:27]=[CH:28][C:29]([Cl:31])=[CH:30][C:25]=3[Cl:24])(=[O:34])=[O:33])[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 81531DiisopropylethylamineHCID 204419Benzenesulfonyl chloride, 2,4-dichloro-HCID 86686890HCID 86686890, compound

Product 1

HCID 86686907HCID 86686907, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a 0° C. solution of (6-fluoro-3-methyl-4-piperidin-4-yl-naphthalen-2-yl)-acetic acid methyl ester (which may be prepared as described above; 110 mg, 0.35 mmol) and 2,4-dichlorobenzenesulfonyl chloride (171 mg, 0.7 mmol) in THF (6.0 mL) was added N,N-diisopropylethylamine (183 μL, 1.05 mmol). The resulting light yellow solution was allowed to warm to room temperature during 2 hours and then it was stirred for 15 hours at room temperature under nitrogen. The reaction mixture was diluted with water and brine solution and the organic compound was extracted into ethyl acetate (2×50 mL). The combined extracts were washed with brine solution and dried over MgSO4. Filtration and concentration gave the crude product which was purified by flash chromatography (40 g ISCO column, eluting with 0-60% ethyl acetate in hexanes) to give {4-[1-(2,4-dichloro-benzenesulfonyl)-piperidin-4-yl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid methyl ester (119 mg, 65%) as an off-white solid. MS cald. for C20H25FNO4S [(M+H)+] 524, obsd. 523.8.

Workup

  1. extractionthe organic compound was extracted into ethyl acetate (2×50 mL)
  2. washThe combined extracts were washed with brine solution
  3. dry with materialdried over MgSO4
  4. filtrationFiltration and concentration
  5. customgave the crude product which
  6. customwas purified by flash chromatography (40 g ISCO column, eluting with 0-60% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-895a75ad84ef464eb270b6a1aa1dc35a
Source dataset
uspto-grants-2014_04
Patent number
US08691993B2

Reaction notes

Loading…