Dimethylamine → 4-amino-3-methoxy-N,N-dimethylbenzamide

Participants

Role	Name	HCID	Charge
Reactant	Dimethylamine	HCID 674	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	2486-69-3	HCID 288057	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	4-amino-3-methoxy-N,N-dimethylbenzamide	HCID 54192364	59.4%

Reaction Steps

HATU (0.296 g, 0.778 mmol) was added to a solution of 4-amino-3-methoxybenzoic acid (0.1 g, 0.598 mmol), DIPEA (0.156 mL, 0.897 mmol) and dimethylamine (2M in THF, 0.598 mL, 1.196 mmol) in THF (1.617 ml). The reaction mixture was stirred for 18 hours. The reaction was partitioned between EtOAc and water, the organic layers were washed with water, dried over Na2SO4 and concentrated in vacuo. The residue was purified by Biotage silica gel column chromatography eluting with DCM/EtOAc 60/40 to 40/60 followed by filtration through an SCX-2 column eluting with 2M NH3/MeOH to afford the title compound as a colourless oil (69 mg, 59%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09409907B2
Source dataset	uspto-grants-2016_08
ORD ID	ord-1949b4effd904a469e618a82708aa7e4
Source note	uspto-grants-2016_08