Dimethylformamide → Trifluoroacetic acid

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	3-amino-N-[3-(trifluoromethyl)phenyl]benzamide	HCID 2317371	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	6H-Pyrrolo[2,3-b]thieno[2,3-d]pyridine-2-carboxylic acid	HCID 57839141	—
Product	Trifluoroacetic acid	HCID 6422	—
Product	HCID 16041280	HCID 16041280	—

Reaction Steps

6H-1-Thia-5,6-diaza-as-indacene-2-carboxylic acid (30 mg, 0.138 mmol) is mixed with DIEA (0.030 ml, 0.172 mmol) and HATU (57.71 mg, 0.151 mmol) in 2 ml DMF at room temperature. 3-Amino-N-(3-trifluoromethyl-phenyl)-benzamide (38.6 mg, 0.138 mmol) is added into the reaction mixture 0.5 hours later. After stirring at room temperature for 2 hours, the reaction mixture is concentrated and purified by Prep-HPLC to afford the title compound as a TFA salt: 1H NMR 400 MHz (DMSO-d6) δ 12.09 (s, 1H), 10.70, (s, 1H), 10.55 (s, 1H), 8.84 (s, 1H), 8.29 (s, 1H), 8.19 (s, 1H), 8.03-7.97 9 (m, 2H), 7.69 (d, 1H, J=7.6 Hz), 7.57-7.49 (m, 3H), 7.40 (d, 1H, J=7.6 Hz), 6.72 (dd, 1H, J=3.2, 1.6 Hz; MS m/z 481.1 (M+1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07589101B2
Source dataset	uspto-grants-2009_09
ORD ID	ord-42b087f50e7b4f319a66fd2a63500bd5
Source note	uspto-grants-2009_09