3-Methoxyaniline → HCID 58711928, compound

HRID 2375024Notes

Reaction equation

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

Participants

Reactant 2

HCID 108243-Methoxyaniline

HCID 58711937HCID 58711937, compound2×

Product 1

HCID 58711928HCID 58711928, compound

Conditions

Temperature: 50 °C

Procedure

A mixture of N-{1-[3-(methylsulfonyl)-1,2,4-triazin-6-yl]ethyl}benzamide (Intermediate 73) (100 mg) and m-anisidine (1 mL) was heated at 50° C. overnight. The crude reaction mixture was then purified by chromatography on silica gel eluting with 30% ethyl acetate in petrol to give N-[1-(3-{[3-(methyloxy)phenyl]amino}-1,2,4-triazin-6-yl)ethyl]benzamide as a yellow solid (35 mg). 1H NMR (CDCl3): δ8.39 (s, 1H), 7.82 (m, 2H), 7.51-7.32 (m, 5H), 7.28-7.13 (m, 3H), 6.68 (m, 1H) 5.47 (m, 1H), 3.84 (s, 3H), 1.70 (d, J=6.9 Hz, 3H).

Workup

customThe crude reaction mixture
customwas then purified by chromatography on silica gel eluting with 30% ethyl acetate in petrol

Sources & evidence

ORD record: ord-823cad7ea1c646d588c4781a8b72360c
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07462614B2

Reaction notes

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