1,7-Dichloroisoquinoline

To a solution of Compound 134C (280 mg, 3.12 mmol) in dry toluene (10 mL) was added DMF (1 mL) and SOCI2 (1 mL) and stirred at 80 C for 3 hours. The reaction mixture was cooled down to room temperature and concentrated under reduced pressure. The residue was purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, from 10% to 30% v/v) to afford Compound 134D. LC-MS (ESI) m/z: 198 [M+H]+. -NMR (CDCh, 400 MHz): (ppm) 7.59 (d, J= 5.6 Hz, 1H), 7.70 (dd, J= 2.4, 8.8 Hz, 1H), 7.81 (d, J= 8.8 Hz, 1H), 8.29 (d, J= 5.6 Hz, 1H), 8.34 (d, J= 1.2 Hz, 1H).General procedure: Pd2(dba)3 (0.1 eq) was added to a solution of appropriate amine (IVc) or (IVd) (ex:3-amino-N-benzylbenzenesulfonamide) (1.1 eq), 1 , 7-Dichloroisoquinoline (II) (800 mg, 4.04 mmol, 1 eq) was added to a heated solution of sulfanilic acid (700 mg, 1 eq) in 50% aq. ethanol (30 mL) at 80 C and reaction mixture was heated at same temperature for 12-15 h. After consumption of starting materials, as observed by TLC, reaction mixture was cooled to room temperature and theresultant precipitate was filtered, and washed with 50% aq. ethanol (5 mL) followed by hot methanol (10 mL) to afford compound 4-(7-chloro-isoquinolin-1-ylamino)-benzenesulfonic acid (XVId) (1.14 g) as a pale yellow solid.Yield: 84%.ES-MS [M-lf: 333.2; tR= 1.47 mm (Method G).?H NMR (400 MHz, DMSO-d6) oe: 8.42 (s, 1H), 7.50 (d, J = 5.6, 1H), 7.38 (d, J = 8.0, 2H), 7.22 (m, 5H), 6.06 (d, J = 5.6 Hz, 1H).General procedure: Following procedure D, as those described in Schemes 1 or 2, compounds offormulae (Vila) or (VIIb) can be prepared in the conditions described below: A mixture of the appropriate chloride (II) (ex:

Molecular Weight:198.05
XLogP3:3.7
Hydrogen Bond Acceptor Count:1
Exact Mass:196.9799046
Monoisotopic Mass:196.9799046
Topological Polar Surface Area:12.9
Heavy Atom Count:12
Complexity:163
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes