Triethylamine → N-Methoxy-2-[3-((E)-2-pyridin-2-yl-vinyl)-1H-indazol-6-ylamino]-benzamide

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	O-Methylhydroxylamine hydrochloride	HCID 521874	—
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	2-[3-(2-Pyridin-2-yl-vinyl)-1H-indazol-6-ylamino]-benzoic acid	HCID 69352963	—
Solvent	Dimethylformamide	HCID 6228	—
Product	N-Methoxy-2-[3-((E)-2-pyridin-2-yl-vinyl)-1H-indazol-6-ylamino]-benzamide	HCID 10317923	67%

Reaction Steps

A solution of 2-[3-(2-Pyridin-2-yl-vinyl)-1H-indazol-6-ylamino]-benzoic acid (50.0 mg, 0.084 mmol), O-methyl-hydroxylamine hydrochloride (15 mg, 0.17 mmol), triethylamine(58 μl, 0.42 mmol), dissolved in DMF (0.8 mL), was treated with HATU (48 mg, 0.13 mmol). The mixture was stirred overnight, then purified by reverse phase HPLC yielding 21.6 mg (67%) of the title compound as a yellow solid. 1H NMR (DMSO-d6): δ 9.23 (1H, s), 8.71 (1H, d, J=2.2), 8.05 (4H, m), 7.51 (5H, m), 7.25 (1H, s), 7.10 (1H, d, J=7.7 Hz), 6.91 (1H, m), 5.98 (1H, m), 4.31 (1H, d, J=14.3), 7.20 (1H, d, J=7.3),4.42 (2H, d, J=3.2). ESIMS (M+H+): 412.1.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07053107B2
Source dataset	uspto-grants-2006_05
ORD ID	ord-80ffb5cc980f412b8d5e4320741ce64d
Source note	uspto-grants-2006_05