Piperidine → HCID 68465797, compound

HRID 506793Notes

Reaction equation

HRID 506793 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]2[N:9]([S:29]([C:32]3[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=3)(=[O:31])=[O:30])[C:10]([C:12]3[C:16]4=[N:17][C:18]([O:23][CH3:24])=[C:19]([O:21][CH3:22])[CH:20]=[C:15]4[N:14]([CH2:25][CH2:26][CH2:27]I)[CH:13]=3)=[CH:11][C:3]=12.[NH:39]1[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1>ClCCl>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]2[N:9]([S:29]([C:32]3[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=3)(=[O:31])=[O:30])[C:10]([C:12]3[C:16]4=[N:17][C:18]([O:23][CH3:24])=[C:19]([O:21][CH3:22])[CH:20]=[C:15]4[N:14]([CH2:25][CH2:26][CH2:27][N:39]4[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]4)[CH:13]=3)=[CH:11][C:3]=12

Participants

4

Reactant 2

HCID 8082PiperidineHCID 68468049HCID 68468049, compound

Product 1

HCID 68465797HCID 68465797, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

a solution of 0.3 g of 3-[4-chloro-5-fluoro-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-1-(3-iodopropyl)-5,6-dimethoxy-1H-pyrrolo[3,2-b]pyridine and 0.382 g of piperidine in 40 cm3 of dichloromethane is refluxed for about 6 hours. After diluting the reaction mixture with 100 cm3 of dichloromethane, the solution is washed with three times 40 cm3 of water, dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (13 kPa). After flash chromatography on a column of silica [eluent: dichloromethane/methanol (98/2 by volume)], 0.175 g of 3-[4-chloro-5-fluoro-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-5,6-dimethoxy-(3-piperidin-1-ylpropyl)-1H-pyrrolo[3,2-b]pyridine is thus obtained as a resin with the following characteristics:

Workup

  1. washthe solution is washed with three times 40 cm3 of water
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to dryness under reduced pressure (13 kPa)

Sources & evidence

ORD record
ord-c63376148135419f9f0a74d2408c31e1
Source dataset
uspto-grants-2010_08
Patent number
US07786114B2

Reaction notes

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