Methylamine → 3-[8-(2,6-difluorophenyl)-2-(4-methyl-1,4'-bipiperidin-1'-yl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-4-yl]-N,4-dimethylbenzamide

Participants

Role	Name	HCID	Charge
Reactant	Methylamine	HCID 6329	—
Reactant	Triethylamine	HCID 8471	—
Reactant	Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 2733084	—
Reactant	HCID 57530509	HCID 57530509	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	3-[8-(2,6-difluorophenyl)-2-(4-methyl-1,4'-bipiperidin-1'-yl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-4-yl]-N,4-dimethylbenzamide	HCID 59212721	22.3%

Reaction Steps

To the compound 3-[8-(2,6-difluorophenyl)-2-(4-methyl-1,4′-bipiperidin-1′-yl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-4-yl]-4-methylbenzoic acid (31.6 mg, 0.055 mmol) in DMF (0.5 mL) were added HBTU (25 mg, 0.066 mmol), triethylamine (15.5 uL, 0.11 mmol) and methylamine (41.3 uL, 0.0825 mmol, 2M soln in THF). The mixture was stirred at rt overnight. Separation by HPLC with TFA, followed by neutralization with SPE amine cartridge afforded the title compound (7.2 mg, 22%). LC-MS m/z 587 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07678801B2
Source dataset	uspto-grants-2010_03
ORD ID	ord-a36a4cb4f01d4c9bb1c1ce84b431782a
Source note	uspto-grants-2010_03