Diisopropylethylamine → N-{2-[(2-Dimethylamino-ethyl)-methyl-amino]-benzothiazol-6-yl}-3-(4-trifluoromethyl-phenyl)-acrylamide

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	4-(Trifluoromethyl)cinnamic acid	HCID 688070	—
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	N2-(2-Dimethylamino-ethyl)-N2-methyl-benzothiazole-2,6-diamine	HCID 55226563	—
Solvent	Methanol	HCID 887	—
Solvent	Dichloromethane	HCID 6344	—
Product	N-{2-[(2-Dimethylamino-ethyl)-methyl-amino]-benzothiazol-6-yl}-3-(4-trifluoromethyl-phenyl)-acrylamide	HCID 68774412	21.2%

Reaction Steps

Prepare according to Method A, using trans-4-trifluoromethylcinnamic acid (130 mg, 0.60 mmol), HATU (229 mg, 0.602 mmol), N2-(2-dimethylamino-ethyl)-N2-methyl-benzothiazole-2,6-diamine (100 mg, 0.400 mmol), DIEA (260 μL, 1.49 mmol), and a chromatography gradient of MeOH in CH2Cl2 (8-20%) to afford the title compound (38 mg, 21%). mass spectrum (m/e): 449.0 [M+H], 447.0 [M−H]. 1H NMR (400 MHz, DMSO-d6): δ 10.50 (s, 1H), 8.31 (d, 1H, J=2.2 Hz), 7.87-7.78 (m, 4H), 7.64 (d, 1H, J=15.8 Hz), 7.52 (dd, 1H, J=8.8, 2.2 Hz), 7.44 (d, 1H, J=8.8 Hz), 7.03 (d, 1H, J=15.8 Hz), 3.97 (dd, 2H, J=6.4, 6.4 Hz), 3.39 (dd, 2H, J=6.2, 6.2 Hz), 3.13 (s, 3H), 2.85 (s, 6H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07838543B2
Source dataset	uspto-grants-2010_11
ORD ID	ord-86ae20dce964483ca460d6035cc45da9
Source note	uspto-grants-2010_11