Dimethylcarbamoyl Chloride → Trifluoroacetic acid

Participants

Role	Name	HCID	Charge
Reactant	Dimethylcarbamoyl Chloride	HCID 6598	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	2-(4-(2,4-difluorophenoxy)piperidin-1-yl)-N-isopropyl-5-methyl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-3-amine TFA salt	HCID 131734032	—
Solvent	Dichloromethane	HCID 6344	—
Product	Trifluoroacetic acid	HCID 6422	191.1%
Product	2-(4-(2,4-difluorophenoxy)piperidin-1-yl)-3-(isopropylamino)-N,N,5-trimethyl-7,8-dihydropyrido[3,4-b]pyrazine-6(5H)-carboxamide	HCID 118159383	—

Reaction Steps

A solution of 2-(4-(2,4-difluorophenoxyl)piperidin-1-yl)-N-isopropyl-5-methyl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-3-amine TFA salt (15 mg, 0.028 mmol), dimethylcarbamic chloride (6.1 mg, 0.056 mmol), and DIPEA (10.9 mg, 0.085 mmol) in DCM (282 μL) was stirred at room temperature overnight. Purification by HPLC Method A afforded the title compound as a TFA salt (6.1 mg) as an off-white film. 1H NMR (500 MHz, methanol-d4) δ ppm 1.26 (dd, J=9.3, 6.4 Hz, 6H), 1.50 (d, J=6.8 Hz, 3H), 1.89-1.98 (m, 2H), 2.12 (dq, J=13.2, 3.6 Hz, 2H), 2.55-2.64 (m, 1H), 2.88 (s, 6H), 2.94-3.03 (m, 3H), 3.34-3.41 (m, 3H), 3.72-3.82 (m, 1H), 4.14 (quin, J=6.5 Hz, 1H), 4.45 (dt, J=7.4, 3.8 Hz, 1H), 4.67 (q, J=6.8 Hz, 1H), 6.83-6.91 (m, 1H), 6.98 (ddd, J=11.4, 8.4, 3.2 Hz, 1H), 7.17 (td, J=9.3, 5.4 Hz, 1H); ESI-MS m/z [M+H]+ 489.90.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09181249B2
Source dataset	uspto-grants-2015_11
ORD ID	ord-9b57329e7246464b91c496567cf9c7c2
Source note	uspto-grants-2015_11