Hydrochloric Acid → 1-(4-Chloro-benzenesulfonyl)-piperidine-3-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide

HRID 336183Notes

Reaction equation

HRID 336183 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:12]([C:16]1[O:20][N:19]=[C:18]([NH:21][C:22]([CH:24]2[CH2:29][CH2:28][CH2:27][NH:26][CH2:25]2)=[O:23])[CH:17]=1)([CH3:15])([CH3:14])[CH3:13].Cl.C(N(CC)C(C)C)(C)C>CN(C=O)C.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[C:12]([C:16]1[O:20][N:19]=[C:18]([NH:21][C:22]([CH:24]2[CH2:29][CH2:28][CH2:27][N:26]([S:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)(=[O:10])=[O:9])[CH2:25]2)=[O:23])[CH:17]=1)([CH3:15])([CH3:13])[CH3:14]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 73984-Chlorobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 58563805Piperidine-3-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide

Product 1

HCID 468721561-(4-Chloro-benzenesulfonyl)-piperidine-3-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-chlorophenylsulfonyl chloride (117.35 mg; 0.556 mmol) in DMF (2 mL) is added piperidine-3-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide; hydrochloride (160 mg; 0.556 mmol), N,N-diisopropylethylamine (0.261 mL; 1.5 mmol) and 4-dimethylaminopyridine (2 mg, 0.016 mmol). The reaction mixture is left stirring at room temperature for 18 hours. After this time, the mixture is diluted with ethyl acetate and washed with water 3 times, then brine, dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography on silica using methanol/methylene chloride provides the title compound, m/z 426/428 [M+H+].

Workup

  1. waitThe reaction mixture is left
  2. washwashed with water 3 times
  3. dry with materialbrine, dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica

Sources & evidence

ORD record
ord-9cc808a8503f4899baf705b2d519f451
Source dataset
uspto-grants-2014_11
Patent number
US08889670B2

Reaction notes

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