(3-Bromo-4-fluorophenyl)methanamine → N-[(3-Bromo-4-fluorophenyl)methyl]-N'-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-1,3-benzenedicarboxamide

Participants

Role	Name	HCID	Charge
Reactant	(3-Bromo-4-fluorophenyl)methanamine	HCID 2724902	—
Reactant	Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 2733084	—
Reactant	3-[({[1,6-Diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoic Acid	HCID 57813277	—
Solvent	Dichloromethane	HCID 6344	—
Product	N-[(3-Bromo-4-fluorophenyl)methyl]-N'-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-1,3-benzenedicarboxamide	HCID 57813256	96%

Reaction Steps

To a solution of 3-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoic acid (500 mg, 1.107 mmol) in DCM (11 mL) was added [(3-bromo-4-fluorophenyl)methyl]amine (266 mg, 1.107 mmol), HBTU (504 mg, 1.329 mmol), and TEA (0.386 mL, 2.77 mmol). This mixture was stirred at room temperature for 18 h before being purified by CombiFlash chromatography to afford 0.6767 g (96%) of the title compound. LC-MS m/z 637 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08067408B2
Source dataset	uspto-grants-2011_11
ORD ID	ord-d86f5d11af51475d8763eae6c78e4a7b
Source note	uspto-grants-2011_11