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 494482Notes

Reaction equation

HRID 494482 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, 2H) 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-83a0718357b34996bbe87c223f37fb0c
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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