Bromine → 6-((S)-2-Amino-3-phenylpropylamino)-3-bromo-2-(4-pyridyl)pyridine

HRID 566710Notes

Reaction equation

HRID 566710 reaction equation
[Br:1]Br.[NH2:3][C@@H:4]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:5][NH:6][C:7]1[N:12]=[C:11]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[CH:10]=[CH:9][CH:8]=1>CC(O)=O>[NH2:3][C@@H:4]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:5][NH:6][C:7]1[N:12]=[C:11]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[C:10]([Br:1])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 158963216-((S)-2-Amino-3-phenylpropylamino)-2-(4-pyridyl)pyridine

Product 1

HCID 158963226-((S)-2-Amino-3-phenylpropylamino)-3-bromo-2-(4-pyridyl)pyridine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A mixture of bromine (1.6 gm, 10 mmole) and HOAc (10 mL) was added in three portions to a stirred solution of 6-((S)-2-Amino-3-phenylpropylamino)-2-(4-pyridyl)pyridine (3.04 gm, 10 mmole) in HOAc (20 mL) at rt. After 1 hr, the mixture was concentrated and purified (SiO2, CH2Cl2/MeOH/NH4OH: 100/11/8) to give 6-((S)-2-Amino-3-phenylpropylamino)-3-bromo-2-(4-pyridyl)pyridine. MS (m/z): Calcd. C19H19N4Br (M+): 383, found : 383.1 and 385.1.

Workup

  1. concentrationthe mixture was concentrated
  2. custompurified (SiO2, CH2Cl2/MeOH/NH4OH: 100/11/8)

Sources & evidence

ORD record
ord-8060ff5c9b4e485fb504e986399b1482
Source dataset
uspto-grants-2001_01
Patent number
US06174901B1

Reaction notes

Loading…