4-Fluorobenzoic Acid → N-[7-(acetyl-methyl-amino)-4-methoxy-benzothiazol-2-yl]-4-fluoro-benzamide

Participants

Role	Name	HCID	Charge
Reactant	4-Fluorobenzoic Acid	HCID 9973	—
Reactant	Diisopropylethylamine	HCID 81531	—
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	N-(2-amino-4-methoxy-benzothiazol-7-yl)-N-methyl-acetamide	HCID 22736969	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	N-[7-(acetyl-methyl-amino)-4-methoxy-benzothiazol-2-yl]-4-fluoro-benzamide	HCID 10237267	24.3%

Reaction Steps

To a stirred solution of 31 mg (0.22 mmol) 4-fluoro-benzoic acid in 2 ml THF were added 89 mg (0.23 mmol) HATU and 0.07 ml (0.44 mmol) N-ethyldiisopropylamine and stirring continued at room temperature for 2 h. 28 mg (0.11 mmol) N-(2-amino-4-methoxy-benzothiazol-7-yl)-N-methyl-acetamide was then added and stirring continued at 50° C. for 16 h. The reaction mixture was then concentrated in vacuo. Flash chromatography (dichloromethane/methanol 50/1) followed by trituration in ether afforded 10 mg (24%) N-[7-(acetyl-methyl-amino)-4-methoxy-benzothiazol-2-yl]-4-fluoro-benzamide as a white crystalline solid. ES-MS m/e (%o): 374 (M+H+, 100).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06713499B2
Source dataset	uspto-grants-2004_03
ORD ID	ord-0b0f7ecae25c451f9a7ec9cddc2bb9d0
Source note	uspto-grants-2004_03