4-Isoquinolinamine

N-(Diphenylmethylene)isoquinolin-4-amine (650 mg, 2.14 mmol) was dissolved in 25 mL tetrahydrofuran and 25 mL ethanol and cooled to 0 °C by using an ice bath. 2M HCl (4.5 mL) was added dropwise at 0° C. The reaction mixture was stirred for another 3 h at room temperature. The reaction mixture was basified by using NaN-(Diphenylmethylene)isoquinolin-4-amine (650 mg, 2.14 mmol) was dissolved in 25 mL tetrahydrofuran and 25 mL ethanol and cooled to 0° C. by using an ice bath. 2M HCl (4.5 mL) was added dropwise at 0° C. The reaction mixture was stirred for another 3 h at room temperature. The reaction mixture was basified by using Na4-Bromo-/5O-quinoline (0.208 g, 1.00 mmol), (CyPF-J-Bu)PdCl4-Bromo-λyoe-quinoline (0.208 g, 1.00 mmol), (CyPF-J-Bu)PdClA mixture of N-benzyl-4-aminoisoquinoline (1.00 gExam le 106Reagents and conditions: (a) Trifluoroacetic anhydride, 100 C, 1 h. (b) Pt02, H2, acetic acid, rt, 10 h. (c) C8H7N02C12, EDCI, HOBt, DIEA, rt. (d) K2C03, aqu. MeOH 80 C. (e) Ci3H10ClN3O2S, DIEA, DMF, 90 C. (f) K2C03, MeOH/water 80 C.[0498] Synthesis of 2-(3, 5-dichlorophenylamino)-l-(4-(7H-pyrrolo[2, 3-J]pyrimidin-4- ylamino)-3, 4-dihydroisoquinolin-2(lH)-yl)ethanone[0499] Synthesis of 2, 2, 2-trifluoro-N-(isoquinolin-4-yl)acetamide: To a solution To a solution of A suspension of 4-bromoisoquinoline (25.0 g), copper(II) sulfate pentahydrate (30.4 g, Nacalai Tesque), 28% aqueous ammonia (100 ml) and 1, 4-dioxane (100 ml) was stirred in a sealed tube at 165 C. for 21 hours. The reaction mixture was cooled to room temperature, the insoluble matters were removed by filtration through Celite, and the filtrate was extracted twice with ethyl acetate (150 ml for each time). The organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=9:1) to obtain the title compound (13.2 g).

Used for synthesis of Rho kinase inhibitors.

Molecular Weight:144.17
XLogP3:1.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:144.068748264
Monoisotopic Mass:144.068748264
Topological Polar Surface Area:38.9
Heavy Atom Count:11
Complexity:136
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes