Sodium t-butoxide → Trifluoroacetic acid

Participants

Role	Name	HCID	Charge
Reactant	Sodium t-butoxide	HCID 23676156	—
Reactant	4-(2,4-Difluorophenoxy)piperidine hydrochloride	HCID 42948943	—
Reactant	6-benzyl-N-(tert-butyl)-3-chloro-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-2-amine TFA salt	HCID 131734016	—
Catalyst	Binap, (A+-)-	HCID 634876	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Toluene	HCID 1140	—
Solvent	Dimethylformamide	HCID 6228	—
Product	Trifluoroacetic acid	HCID 6422	483.8%
Product	6-benzyl-N-(tert-butyl)-3-(4-(2,4-difluorophenoxy)piperidin-1-yl)-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-2-amine	HCID 118159278	—

Reaction Steps

A solution of sodium tert-butoxide (81 mg, 0.843 mmol), 6-benzyl-N-(tert-butyl)-3-chloro-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-2-amine TFA salt (125 mg, 0.281 mmol), Pd2(dba)3 (12.86 mg, 0.014 mmol), 4-(2,4-difluorophenoxyl)piperidine hydrochloride (84 mg, 0.337 mmol), and BINAP (17.50 mg, 0.028 mmol) in toluene (937 μL) was stirred at 90° C. overnight. The crude reaction mixture was diluted in DMF, filtered through a hydrophilic PTFE 0.45 μm filter (Millipore® Millex-LCR), and purified via HPLC Method A to give 6-benzyl-N-(tert-butyl)-3-(4-(2,4-difluorophenoxyl)piperidin-1-yl)-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-2-amine as a TFA salt (155 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09181249B2
Source dataset	uspto-grants-2015_11
ORD ID	ord-7295972bb4924c94a95f7b2c97f1bcfa
Source note	uspto-grants-2015_11