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

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	3-(4-Fluorophenyl)-2-propenoic acid	HCID 98070	—
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-fluoro-phenyl)-acrylamide	HCID 68775363	11.3%

Reaction Steps

Prepare according to Method A, using 4-fluorocinnamic acid (100 mg, 0.602 mmol), HATU (228 mg, 0.600 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 yield the title compound (18 mg, 11%). mass spectrum (m/e): 399.0 [M+H]. 1H NMR (400 MHz, DMSO-d6): δ 10.38 (s, 1H), 8.30 (d, 1H, J=1.8 Hz), 7.72-7.66 (m, 2H), 7.57 (d, 1H, J=15.8 Hz), 7.50 (dd, 1H, J=8.8, 2.2 Hz), 7.43 (d, 1H, J=8.8 Hz), 7.32-7.25 (m, 2H), 6.84 (d, 1H, J=15.8 Hz), 3.95 (dd, 2H, J=6.4, 6.4 Hz), 3.39-3.33 (m, 2H), 3.13 (s, 3H), 2.83 (s, 6H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07838543B2
Source dataset	uspto-grants-2010_11
ORD ID	ord-84596d9dd9904f8baea2c3c0e4ce35c6
Source note	uspto-grants-2010_11