2,4-Dimethoxybenzylamine → 4-(4-aminonaphthalen-1-ylthio)-N-(2,4-dimethoxybenzyl)pyridin-2-amine

HRID 571109Notes

Reaction equation

HRID 571109 reaction equation
Cl[C:2]1[CH:7]=[C:6]([S:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([NH2:19])=[CH:11][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[CH3:20][O:21][C:22]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:23]=1[CH2:30][NH2:31]>>[NH2:19][C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]([S:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:31][CH2:30][C:23]3[CH:24]=[CH:25][C:26]([O:28][CH3:29])=[CH:27][C:22]=3[O:21][CH3:20])[CH:7]=2)=[CH:10][CH:11]=1

Participants

3

Reactant 2

HCID 5972502,4-DimethoxybenzylamineHCID 866767494-(2-Chloropyridin-4-ylthio)naphthalen-1-amine

Product 1

HCID 674584834-(4-aminonaphthalen-1-ylthio)-N-(2,4-dimethoxybenzyl)pyridin-2-amineYield 38.6%

Conditions

Temperature
120 °C

Procedure

A mixture of 4-(2-chloropyridin-4-ylthio)naphthalen-1-amine (1.40 g, 90% purity, 4.40 mmol) and (2,4-dimethoxyphenyl)methanamine (3.7 mL, 24 mmol) was heated together at 120° C. for 24 hr. The reaction mixture was loaded directly onto silica and purified by flash column chromatography (SiO2, 80 g, EtOAc in isohexane, 30-70%, gradient elution) to afford 4-(4-aminonaphthalen-1-ylthio)-N-(2,4-dimethoxybenzyl)pyridin-2-amine as a dark red oil (710 mg, 37%); Rt 1.74 min (Method 2); m/z 418 (M+H)+ (ES+).

Workup

  1. custompurified by flash column chromatography (SiO2, 80 g, EtOAc in isohexane, 30-70%, gradient elution)

Sources & evidence

ORD record
ord-2e74ffccec79484db0863d4c62876c19
Source dataset
uspto-grants-2015_05
Patent number
US09024041B2

Reaction notes

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