3-Acetamidobenzoic acid → 3-(acetylamino)-N-(1-(3-[(3,4,5-trimethoxyphenyl)amino]-1,2,4-triazin-6-yl}ethyl)benzamide

Participants

Role	Name	HCID	Charge
Reactant	3-Acetamidobenzoic acid	HCID 48847	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	6-(1-aminoethyl)-N-(3,4,5-trimethoxyphenyl)-1,2,4-triazin-3-amine	HCID 53404429	—
Reactant	3-bromo-N-(1-{3-[(3,4,5-trimethoxyphenyl)amino]-1,2,4-triazin-6-yl}ethyl)benzamide	HCID 58711954	—
Solvent	Dimethylformamide	HCID 6228	—
Product	3-(acetylamino)-N-(1-(3-[(3,4,5-trimethoxyphenyl)amino]-1,2,4-triazin-6-yl}ethyl)benzamide	HCID 58711946	75%

Reaction Steps

In a similar manner as described for Intermediate 18, 6-(1-aminoethyl)-N-(3,4,5-trimethoxyphenyl)-1,2,4-triazin-3-amine (Intermediate 9) (113 mg, 0.33 mmol), 3-(acetylamino)benzoic acid (110 mg, 0.61 mmol), diisopropylethylamine (0.40 mL, 2.3 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (252 mg, 0.66 mmol) in dimethylformamide (2 mL) gave 3-(acetylamino)-N-(1-{3-[(3,4,5-trimethoxyphenyl)amino]-1,2,4-triazin-6-yl}ethyl)benzamide (116 mg, 75%) as a yellow solid. MS m/z 466 (M+1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07462614B2
Source dataset	uspto-grants-2008_12
ORD ID	ord-2e1b72e1a73a4bb5bb21ba8b6208302c
Source note	uspto-grants-2008_12