Hydrochloric Acid → HCID 46872269, compound

HRID 336182Notes

Reaction equation

HRID 336182 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Cl)=[CH:4][CH:3]=1.[C:10]([C:14]1[O:18][N:17]=[C:16]([NH:19][C:20]([CH:22]2[CH2:27][CH2:26][CH2:25][NH:24][CH2:23]2)=[O:21])[CH:15]=1)([CH3:13])([CH3:12])[CH3:11].Cl.C(N(CC)C(C)C)(C)C>CN(C=O)C.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[C:10]([C:14]1[O:18][N:17]=[C:16]([NH:19][C:20]([CH:22]2[CH2:27][CH2:26][CH2:25][N:24]([CH2:6][C:5]3[CH:8]=[CH:9][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH2:23]2)=[O:21])[CH:15]=1)([CH3:13])([CH3:11])[CH3:12]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 81531DiisopropylethylamineHCID 58563805Piperidine-3-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide

Product 1

HCID 46872269HCID 46872269, compound

Reagents, catalysts & solvents 3

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

Procedure

To a solution of 4-chlorobenzyl chloride (134 mg; 0.832 mmol) in DMF (3 mL) is added piperidine-3-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide; hydrochloride (238.86 mg; 0.83 mmol) and N,N-diisopropylethylamine (0.331 mL; 1.9 mmol). The reaction mixture is left stirring at room temperature for 18 hours in the presence of catalytic amount of 4-dimethylaminopyridine (1 mg). 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 376/378 [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-3639f4e3ea084386b094c911cddb6cd8
Source dataset
uspto-grants-2014_11
Patent number
US08889670B2

Reaction notes

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