(2S)-3-Phenylpropane-1,2-diamine → 6-((S)-2-Amino-3-phenylpropylamino)-2-(4-pyridyl)pyridine

HRID 566709Notes

Reaction equation

HRID 566709 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[CH:5]=[CH:4][CH:3]=1.[NH2:14][C@@H:15]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:16][NH2:17]>>[NH2:14][C@@H:15]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:16][NH:17][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 12699301(2S)-3-Phenylpropane-1,2-diamineHCID 135464536-Bromo-2,4'-bipyridine

Product 1

HCID 158963216-((S)-2-Amino-3-phenylpropylamino)-2-(4-pyridyl)pyridine

Conditions

Temperature
190 °C

Procedure

A neat mixture of 6-bromo-[2,4′]bipyridine (2.35 gm, 10 mmole) and (S)-2-amino-3-phenylpropylamine (3 gm, 20 mmole) was heated to 190° C. for 4 hr. The reaction was cooled to rt and purified (SiO2, CH2Cl2/MeOH/NH4OH: 100/11/8) to give the step 1 compound. (This reaction provides major products wherein the less hindered amine functionality displaces the bromide,when the nucleophile is an alkyldiamine) MS (m/z): Calcd. C19H20N4 (M+): 304, found (M+H)+: 305.2.

Workup

  1. temperatureThe reaction was cooled to rt
  2. custompurified (SiO2, CH2Cl2/MeOH/NH4OH: 100/11/8)
  3. customto give the step 1 compound
  4. custom(This reaction provides major products wherein the

Sources & evidence

ORD record
ord-3f0489ca7fcf43a887e8e799b082e009
Source dataset
uspto-grants-2001_01
Patent number
US06174901B1

Reaction notes

Loading…