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

HRID 2224803Notes

Reaction equation

HRID 2224803 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]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 136384912Tert-butyl 3-(7-fluoro-1-hydroxy-3-oxo-4,4-dipropyl-3,4-dihydronaphthalen-2-yl)-1,1-dioxido-4h-1,2,4-benzothiadiazin-7-ylcarbamate

Product 1

HCID 1363756033-(7-amino-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)-6-fluoro-4-hydroxy-1,1-dipropylnaphthalen-2(1H)-oneYield 107.7%

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).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. stirringthe residue was stirred with ethyl acetate and saturated sodium bicarbonate solution for 30 min
  3. extractionThe organic layer was extracted with saturated NaCl solution
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a167fa4d0f464c16aa7ad5bcf884399e
Source dataset
uspto-grants-2008_05
Patent number
US07378414B2

Reaction notes

Loading…