HCID 67195083, compound → HCID 67192905, compound

HRID 551289Notes

Reaction equation

HRID 551289 reaction equation
[ClH:1].[C:2]1([C:8]#[C:9][C:10]2[CH:11]=[C:12]([C:16]([N:18]3[CH2:23][CH2:22][CH:21]([C:24]4[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=4)[C:27]([NH2:29])=[NH:28])[CH2:20][CH2:19]3)=[O:17])[CH:13]=[N:14][CH:15]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.[Pd]>[ClH:1].[C:2]1([CH2:8][CH2:9][C:10]2[CH:11]=[C:12]([C:16]([N:18]3[CH2:19][CH2:20][CH:21]([C:24]4[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=4)[C:27]([NH2:29])=[NH:28])[CH2:22][CH2:23]3)=[O:17])[CH:13]=[N:14][CH:15]=2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 67195083HCID 67195083, compound

Product 1

HCID 67192905HCID 67192905, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-[1-(5-phenylethynyl-pyridine-3-carbonyl)-piperidin-4-yl]-benzamidine hydrochloride (Example 46) (150 mg) in ethanol (5 ml), treated with 10% palladium on carbon (15 mg) and stirred at ambient temperature under an atmosphere of hydrogen for 5 hours. The reaction mixture is filtered through a short pad of hyflo and concentrated under vacuum to give the title compound as a colourless oil (150 mg). 1H NMR (DMSO, 500 MHz) δ8.48 (m, 2H), 7.78 (s, 1H), 7.65 (m, 3H), 7.59 (m, 1H), 7.20 (m, 5H), 4.63 (br m, 1H), 3.57 (br m, 1H), 3.18 (br m, 1H), 2.90 (m, 6H), 1.70-1.90 (br m, 4H). EI MS M++H: 413.

Workup

  1. filtrationThe reaction mixture is filtered through a short pad of hyflo
  2. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ab81bce1545d421eb7698e80f519337b
Source dataset
uspto-grants-2011_05
Patent number
US07947684B2

Reaction notes

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