Trifluoroacetic acid → 3-(7-amino-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)-6-fluoro-4-hydroxy-1,1-dipropylnaphthalen-2(1H)-one
Reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH2:37][CH2:38][CH3:39])([CH2:34][CH2:35][CH3:36])[C:7](=[O:33])[C:8]([C:13]3[NH:18][C:17]4[CH:19]=[CH:20][C:21]([NH:23]C(=O)OC(C)(C)C)=[CH:22][C:16]=4[S:15](=[O:32])(=[O:31])[N:14]=3)=[C:9]2[OH:12])=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>>[NH2:23][C:21]1[CH:20]=[CH:19][C:17]2[NH:18][C:13]([C:8]3[C:7](=[O:33])[C:6]([CH2:34][CH2:35][CH3:36])([CH2:37][CH2:38][CH3:39])[C:5]4[C:10]([C:9]=3[OH:12])=[CH:11][C:2]([F:1])=[CH:3][CH:4]=4)=[N:14][S:15](=[O:31])(=[O:32])[C:16]=2[CH:22]=1Participants
3
Reactant 2
Product 1
Procedure
The compound of Example 17B (76 mg, 0.14 mmol) was added to trifluoroacetic acid (6 mL) and stirred at ambient temperature for 30 min. The solution was concentrated in vacuo and the residue was stirred with ethyl acetate and saturated sodium bicarbonate solution for 30 min. The organic layer was extracted with saturated NaCl solution, dried (Na2SO4) and concentrated in vacuo to afford the title compound (69 mg, 100%) as a foam. 1H NMR (300 MHz, DMSO-d6): δ 0.62 (m, 8 H) 0.86 (dd, J=12.32, 6.43 Hz, 2 H) 2.00 (s, 2 H) 2.16 (m, 2 H) 6.96 (m, 2 H) 7.43 (d, J=8.82 Hz, 1 H) 7.63 (m, 1 H) 7.82 (m, 2 H) 13.48 (s, 1 H).