2-Aminobenzo[b]thiophene

b; 1-Benzothiophen-2-amine[00118] To a solution of 1 , 1-Dimethylethyl 1-benzothien-2-ylcarbamate (1.0 g, 4.01 mmoles) in DCM (10 ml_) was added TFA (2.0 mL) and stirred for 12 h. The reaction mixture was concentrated, and the resulted residue was redissolved in DCM and washed with 1 N NaOH (2x50 mL), brine and dried over NaA solution of compound 235 (0.250 g, 1.00 mmol) was stirred in 4 M HCl solution in 1, 4-dioxane (3 mL) at room temperature for 2 hrs at which time thin layer chromatography (DCM/Hexanes) indicated the reaction was complete. The reaction mixture was cooled to room temperature and concentrated under vacuum. The residue was diluted with acetonitrile, sonicated, and concentrated to afford compound 236 as a grey solid 0.24 g (91percent). HPLC-MS tExample 236; A solution of compound 235 (0.250 g, 1.00 mmol) was stirred in 4 M HCl solution in 1, 4-dioxane (3 mL) at room temperature for 2 hrs at which time thin layer chromatography (DCM/Hexanes) indicated the reaction was complete. The reaction mixture was cooled to room temperature and concentrated under vacuum. The residue was diluted with acetonitrile, sonicated, and concentrated to afford compound 236 as a grey solid 0.24 g (91percent). HPLC-MS t10.0 g (76.9 mmol) of Carboxylic acid (2 mmol, 1 equiv.) and HATU (76 mg, 0.2 mmol, 1 equiv.) were dissolved in 1 mL DCE in a one dram vial charged with a stir bar. DIPEA (0.1 mL, 0.6 mmol, 3 equiv.) was added and the resulting solution was stirred at RT for 10 minutes. Amine (0.2 mmol, 1 equiv.) was added to the mixture. The reaction solution was heated to 45 C and stirred overnight. Upon completion the reaction mixture was condensed and loaded onto a 60g C-18 cartridge and purified over a gradient of 5-95% ACN:H20. The fractions containing product were identified by LC-MS and condensed in vauco to give the final product.

Molecular Weight:149.21
XLogP3:2.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:149.02992040
Monoisotopic Mass:149.02992040
Topological Polar Surface Area:54.3
Heavy Atom Count:10
Complexity:126
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes