반응 #1890446

반응 방정식

N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-4-(4-fluorophenyl)-5,7-dihydro-4H-spiro[benzo[d]thiazole-6,2′-[1,3]dioxolan]-2-amine

HCl

→

desired product

2-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenylamino)-4-(4-fluorophenyl)-4,5-dihydrobenzo[d]thiazol-6(7H)-one

용매

acetone

반응 조건

후처리

1. 1
   온도was heated
2. 2
   온도at reflux for 24 h

실험 절차

A mixture of N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-4-(4-fluorophenyl)-5,7-dihydro-4H-spiro[benzo[d]thiazole-6,2′-[1,3]dioxolan]-2-amine (54 mg, 0.105 mmol, example 74), aqueous 1.0 M HCl (0.16 mL), and acetone (0.13 mL) was heated at reflux for 24 h. Partial conversion of the starting material to the desired product was evident by LCMS analysis of a crude aliquot. An additional portion of aqueous 1.0 M HCl (0.20 mL) was added and the acetone was removed in vacuo. The resulting mixture was heated at 75° C. for an additional 24 h. The crude reaction was quenced with saturated sodium bicarbonate solution and extracted with EtOAc. The organic layer was concentrated in vacuo. The crude product was purified using preparatory TLC (50% acetone/hexanes) to give 22 mg (43% yield) of the titled compound as an oil. LC-MS (M+H)+ 469.2. 1H NMR (400 MHz, chloroform-d) δ ppm 7.54 (d, J=1.51 Hz, 1 H) 7.46 (d, J=2.52 Hz, 1 H) 7.09-7.20 (m, 3 H) 6.94-7.07 (m, 3 H) 6.77 (dd, J=8.44, 2.39 Hz, 1 H) 4.46 (t, J=6.42 Hz, 1 H) 3.63-3.67 (m, 2 H) 3.62 (s, 3 H) 3.08 (dd, J=14.35, 6.55 Hz, 1 H) 2.86 (dd, J=14.23, 6.42 Hz, 1 H).

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