Ethanol → HCID 58281292, compound

HRID 552316Notes

Reaction equation

HRID 552316 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N:9]2[C:13]3=[N:14][C:15]([CH3:28])=[CH:16][C:17]([N:18]4[CH2:23][CH2:22][CH:21]([CH2:24][C:25]([OH:27])=[O:26])[CH2:20][CH2:19]4)=[C:12]3[C:11]([CH3:29])=[CH:10]2)=[C:4]([CH3:30])[CH:3]=1.[CH2:31](O)[CH3:32].Cl.CN(C)CCCN=C=NCC.CN(C1C=CC=CN=1)C>C(Cl)(Cl)Cl.O.C(OCC)(=O)C>[CH2:31]([O:26][C:25](=[O:27])[CH2:24][CH:21]1[CH2:20][CH2:19][N:18]([C:17]2[CH:16]=[C:15]([CH3:28])[N:14]=[C:13]3[N:9]([C:5]4[C:6]([CH3:8])=[CH:7][C:2]([Br:1])=[CH:3][C:4]=4[CH3:30])[CH:10]=[C:11]([CH3:29])[C:12]=23)[CH2:23][CH2:22]1)[CH3:32]

Participants

8

Reactant 4

HCID 702EthanolHCID 218852-DimethylaminopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11547298HCID 11547298, compound

Product 1

HCID 58281292HCID 58281292, compoundYield 93.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 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. customseparated
  2. washThe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified with column chromatography (silica gel: Wako gel C200, eluent: hexane:ethyl acetate=4/1)

Sources & evidence

ORD record
ord-d7c5b5a983244ca1a14dbac60cf04f24
Source dataset
uspto-grants-2011_05
Patent number
US07951811B2

Reaction notes

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