Sodium borohydride → 2-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenylamino)-4-(4-fluorophenyl)-4,5,6,7-tetrahydrobenzo[d]thiazol-6-ol

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Reaction Steps

A mixture of 2-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenylamino)-4-(4-fluorophenyl)-4,5-dihydrobenzo[d]thiazol-6(7H)-one (5.0 mg, 0.011 mmol, from example 75), sodium borohydride (1.2 mg, 0.032 mmol), and methanol (0.050 mL) were stirred at rt for 1 h. The crude reaction was quenched with brine solution and extracted with EtOAc. The organic layer was concentrated in vacuo to afford 4.0 mg (76% yield) of the titled compound as a brown oil. LC-MS (M+H)+ 471.2. 1H NMR (400 MHz, methanol-d4) δ ppm 7.82 (d, J=2.01 Hz, 1 H) 7.63 (d, J=1.51 Hz, 1H) 7.33 (s, 1 H) 7.17-7.24 (m, 3 H) 7.13 (d, J=8.56 Hz, 1 H) 7.02 (t, J=8.81 Hz, 2 H) 6.64 (dd, J=8.56, 2.27 Hz, 1 H) 4.00-4.23 (m, 3 H) 3.33 (s, 3 H) 3.04 (dd, J=15.23, 5.41 Hz, 1 H) 2.70 (ddd, J=15.30, 9.76, 3.15 Hz, 1 H) 2.29-2.42 (m, 1 H).

Provenance & Evidence