Hydrochloric Acid → HCID 67152637, compound

HRID 552317Notes

Reaction equation

HRID 552317 reaction equation
[CH2:1]([O:3][C:4](=[O:32])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[C:16]([CH3:18])[N:15]=[C:14]3[N:19]([C:23]4[C:28]([CH3:29])=[CH:27][C:26]([Br:30])=[CH:25][C:24]=4[CH3:31])[CH:20]=[C:21]([CH3:22])[C:13]=23)[CH2:8][CH2:7]1)[CH3:2].[ClH:33]>C(O)C.C(OCC)(=O)C>[ClH:33].[CH2:1]([O:3][C:4](=[O:32])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[C:16]([CH3:18])[N:15]=[C:14]3[N:19]([C:23]4[C:28]([CH3:29])=[CH:27][C:26]([Br:30])=[CH:25][C:24]=4[CH3:31])[CH:20]=[C:21]([CH3:22])[C:13]=23)[CH2:8][CH2:7]1)[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58281292HCID 58281292, compound

Product 1

HCID 67152637HCID 67152637, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of {1-[1-(4-bromo-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-acetic acid (100 mg) in CHCl3 (4 mL) in an ice cooling bath was added ethanol (20 mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (61 mg), and dimethylaminopyridine (26 mg), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into ethyl acetate and water, and separated. The organic phase was washed with brine, dried over Na2SO4, and filtered. The filtrate was concentrated under reduced pressure and the residue was purified with column chromatography (silica gel: Wako gel C200, eluent: hexane:ethyl acetate=4/1) to obtain {1-[1-(4-bromo-2,6-dimethylphenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]piperidin-4-yl}acetic acid ethyl ester (99 mg). {1-[1-(4-Bromo-2,6-dimethylphenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]piperidin-4-yl}acetic acid ethyl ester was dissolved in ethanol (2 mL) and 4 M HCl in ethyl acetate solution (60 μL) was added into the solution with cooling in an ice bath. After stirring at room temperature, the reaction mixture was concentrated under reduced pressure, and the residue was crystallized from diisopropylether (1 mL). The crystal was collected by filtration to obtain the title compound. (95 mg)

Workup

  1. temperaturewith cooling in an ice bath
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customthe residue was crystallized from diisopropylether (1 mL)
  4. filtrationThe crystal was collected by filtration

Sources & evidence

ORD record
ord-b03b312eebc446ab94be2ff70944e151
Source dataset
uspto-grants-2011_05
Patent number
US07951811B2

Reaction notes

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