1-(3-Bromopropyl)-4-methoxybenzene → {2-[(3,5-Diamino-6-chloro-pyrazine-2-carbonyl)-amino]-ethyl}-[3-(4-methoxy-phenyl)-propyl]-dimethyl-ammonium bromide

HRID 882892Notes

Reaction equation

HRID 882892 reaction equation
[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[C:13]([NH2:14])=[N:12][C:11]([NH2:15])=[C:10]([Cl:16])[N:9]=1)=[O:7].[Br:18][CH2:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1>CC(C)=O>[Br-:18].[NH2:14][C:13]1[C:8]([C:6]([NH:5][CH2:4][CH2:3][N+:2]([CH2:19][CH2:20][CH2:21][C:22]2[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=2)([CH3:17])[CH3:1])=[O:7])=[N:9][C:10]([Cl:16])=[C:11]([NH2:15])[N:12]=1

Participants

4

Reactant 2

HCID 127769961-(3-Bromopropyl)-4-methoxybenzeneHCID 151481303,5-Diamino-6-chloro-N-[2-(dimethylamino)ethyl]-2-pyrazinecarboxamide2×

Product 1

HCID 56951058{2-[(3,5-Diamino-6-chloro-pyrazine-2-carbonyl)-amino]-ethyl}-[3-(4-methoxy-phenyl)-propyl]-dimethyl-ammonium bromide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture comprising 3,5-diamino-6-chloro-pyrazine-2-carboxylic acid (2-dimethylamino-ethyl)-amide (Intermediate H) (1.8 g, 7.0 mmol) and 1-(3-bromo-propyl)-4-methoxy-benzene (3.2 g, 14.0 mmol) in acetone (50 mL) is heated at reflux for 72 h. After cooling to RT, the solvent is removed in vacuo and the resulting solid is recrystallised from ethanol to afford the title compound. M+ 407. 1H NMR (400 MHz, DMSO-d6) δ 8.37 (1H, t), 7.76 (2H, br), 7.19 (2H, br), 7.17 (2H, d), 6.90 (2H, d), 3.79 (3H, s), 3.67 (2H, q), 3.49 (2H, t), 3.15 (6H, s), 2.55 (2H, t), 2.02 (2H, quintet).

Workup

  1. temperatureat reflux for 72 h
  2. customthe solvent is removed in vacuo
  3. customthe resulting solid is recrystallised from ethanol

Sources & evidence

ORD record
ord-bf9a1078f06946adbd22a7d4d0e6eb17
Source dataset
uspto-grants-2012_08
Patent number
US08236808B2

Reaction notes

Loading…