HCID 69030762, compound → HCID 86589764, compound

HRID 489596Notes

Reaction equation

HRID 489596 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]([C:17]2[CH2:18][CH2:19][N:20]([C:23]([C:25]3[CH:26]=[N:27][CH:28]=[C:29]([CH2:31][CH2:32][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[CH:30]=3)=[O:24])[CH2:21][CH:22]=2)[CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]([CH:17]2[CH2:18][CH2:19][N:20]([C:23]([C:25]3[CH:26]=[N:27][CH:28]=[C:29]([CH2:31][CH2:32][C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)[CH:30]=3)=[O:24])[CH2:21][CH2:22]2)[CH:11]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 69030762HCID 69030762, compound

Product 1

HCID 86589764HCID 86589764, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of N-(tert-butoxycarbonyl)-4-fluoro-3-[1-(5-phenylethyl-pyridine-3-carbonyl)-1,2,3,6-tetrahydro-pyridin-4-yl]-benzylamine in ethanol (12 ml) was treated with 10% palladium on carbon (75 mg) and the mixture was stirred at ambient temperature under an atmosphere of hydrogen for 72 hours. The reaction mixture was filtered through a short pad of hyflo and the filtrate was concentrated under vacuum to give N-(tert-butoxycarbonyl-4-fluoro-3-[1-(5-phenylethyl-pyridine-3-carbonyl)-piperidin-4-yl]-benzylamine as colorless oil (85 mg). This material was dissolved in methanol (10 ml) and the solution was cooled to 0° C. and then saturated with hydrogen chloride gas. This mixture was stirred at ambient temperature for 4 hours and then concentrated to dryness under vacuum. The residue was triturated with a mixture of dichloromethane and diethyl ether to give 4-fluoro-3-[1-(5-phenylethyl-pyridine-3-carbonyl)-piperidin-4-yl]-benzylamine di-hydrochloride as a white amorphous solid (50 mg). 1H NMR [(CD3)2SO, 500 MHz]: δ 8.60 (s, 1H), 8.58 (s, 1H), 7.83 (s, 1H), 7.60 (m, 1H), 7.38 (m, 1H), 7.20 (m, 6H), 4.61 (br m, 1H), 4.00 (m, 2H), 3.50 (br m, 1H), 3.20 (br m, 2H), 2.99 (m, 2H), 2.95 (m, 2H), 2.90 (br m, 1H), 1.82 (br m, 1H), 1.65 (br m, 3H). MS(EI): 418(M++H).

Workup

  1. filtrationThe reaction mixture was filtered through a short pad of hyflo
  2. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-834af2cb77d142b9b67d85bf34f19953
Source dataset
uspto-grants-2005_12
Patent number
US06977263B2

Reaction notes

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