ethyl (7-hydroxy-8-nitro-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)acetate → ethyl (8-amino-7-hydroxy-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)acetate

HRID 601337Notes

Reaction equation

HRID 601337 reaction equation
[OH:1][C:2]1[CH:19]=[CH:18][C:5]2[NH:6][C:7]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:8][S:9](=[O:11])(=[O:10])[C:4]=2[C:3]=1[N+:20]([O-])=O.[H][H]>CO.[Pd]>[NH2:20][C:3]1[C:4]2[S:9](=[O:11])(=[O:10])[N:8]=[C:7]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[NH:6][C:5]=2[CH:18]=[CH:19][C:2]=1[OH:1]

Participants

5

Reactant 2

HCID 86594015ethyl (7-hydroxy-8-nitro-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 86594014ethyl (8-amino-7-hydroxy-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)acetateYield 99.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The product of Example 352D (61 mg, 0.1852 mmol) in methanol (5 mL) was hydrogenated at 1 atmosphere hydrogen pressure (balloon) with 10% palladium on carbon (9 mg, 15 weight %) for 45 minutes. The reaction was filtered through a PTFE membrane filter (0.45 μm) and the catalyst thoroughly washed with warm methanol (50 mL). The filtrate was concentrated under reduced pressure to give the title compound as a beige solid (55 mg, 99%). MS (ESI−) m/z 298 (M−H)−. 1H NMR (300 MHz, DMSO-d6) δ 1.21 (t, J=7.17 Hz, 3 H) 3.61 (s, 2 H) 4.15 (q, J=6.99 Hz, 2 H) 5.22 (s, 2 H) 6.40 (d, J=8.46 Hz, 1 H) 6.93 (d, J=8.46 Hz, 1 H) 9.82 (s, 1 H) 11.86 (s, 1 H).

Workup

  1. filtrationThe reaction was filtered through a PTFE membrane
  2. filtrationfilter (0.45 μm)
  3. washthe catalyst thoroughly washed with warm methanol (50 mL)
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1c9a244821744385971f2e5e6a55f514
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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