4-(6-Bromo-[1,8]naphthyridin-2-yl)piperidin-1-yl-carbonyl-2-(S)-phenylsulfonylamino-beta-alanine t-butyl ester → 4-(5,6,7,8-Tetrahydro-[1,8]naphthyridin-2-yl)piperidin-1-yl-carbonyl-2-(S)-phenylsulfonylamino-beta-alanine t-butyl ester

HRID 580907Notes

Reaction equation

HRID 580907 reaction equation
[C:1]([O:5][C:6](=[O:39])[C@@H:7]([NH:29][S:30]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)(=[O:32])=[O:31])[CH2:8][NH:9][C:10]([N:12]1[CH2:17][CH2:16][CH:15]([C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[N:21][CH:22]=[C:23](Br)[CH:24]=3)[N:19]=2)[CH2:14][CH2:13]1)=[O:11])([CH3:4])([CH3:3])[CH3:2]>[Pd].CCO>[C:1]([O:5][C:6](=[O:39])[C@@H:7]([NH:29][S:30]([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)(=[O:31])=[O:32])[CH2:8][NH:9][C:10]([N:12]1[CH2:13][CH2:14][CH:15]([C:18]2[CH:27]=[CH:26][C:25]3[CH2:24][CH2:23][CH2:22][NH:21][C:20]=3[N:19]=2)[CH2:16][CH2:17]1)=[O:11])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 867541534-(6-Bromo-[1,8]naphthyridin-2-yl)piperidin-1-yl-carbonyl-2-(S)-phenylsulfonylamino-beta-alanine t-butyl ester

Product 1

HCID 867541524-(5,6,7,8-Tetrahydro-[1,8]naphthyridin-2-yl)piperidin-1-yl-carbonyl-2-(S)-phenylsulfonylamino-beta-alanine t-butyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of bromide 3-6 (125 mg, 0.2021 mmol), 10% Pd/C (125 mg) and EtOH (5 ml) was stirred under 1 atm H2 for 1.0 h. The reaction mixture was then filtered through a celite pad and the filtrate concentrated to give urea 3-7 as a colorless oil.

Workup

  1. filtrationThe reaction mixture was then filtered through a celite pad
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-b9ca9e98237749c89ea1a49b6822c851
Source dataset
uspto-grants-1999_07
Patent number
US05919792

Reaction notes

Loading…