Sodium Bicarbonate → sodium (S)-4-amino-5-((1-(3-methylbutanoyl)piperidin-3-yl)methoxy)benzo[c][1,2,6]thiadiazin-1-ide 2,2-dioxide

HRID 2280180Notes

Reaction equation

HRID 2280180 reaction equation
[NH2:1][C:2]1[C:3]2[C:13]([O:14][CH2:15][C@H:16]3[CH2:21][CH2:20][CH2:19][N:18]([C:22](=[O:27])[CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:17]3)=[CH:12][CH:11]=[CH:10][C:4]=2[NH:5][S:6](=[O:9])(=[O:8])[N:7]=1.C([O-])(O)=O.[Na+:32]>O>[NH2:1][C:2]1[C:3]2[C:13]([O:14][CH2:15][C@H:16]3[CH2:21][CH2:20][CH2:19][N:18]([C:22](=[O:27])[CH2:23][CH:24]([CH3:25])[CH3:26])[CH2:17]3)=[CH:12][CH:11]=[CH:10][C:4]=2[N-:5][S:6](=[O:8])(=[O:9])[N:7]=1.[Na+:32]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 73213585(S)-1-(3-(((4-Amino-2,2-dioxido-1H-benzo(c)(1,2,6)thiadiazin-5-yl)oxy)methyl)piperidin-1-yl)-3-methylbutan-1-one

Product 1

HCID 86714321sodium (S)-4-amino-5-((1-(3-methylbutanoyl)piperidin-3-yl)methoxy)benzo[c][1,2,6]thiadiazin-1-ide 2,2-dioxideYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of (S)-1-(3-(((4-amino-2,2-dioxido-1H-benzo[c][1,2,6]thiadiazin-5-yl)oxy)methyl)piperidin-1-yl)-3-methylbutan-1-one (2.0 g, 5.07 mmol) (Example 5) in water (25 mL), was added NaHCO3 (425 mg, 5.07 mmol). The reaction was heated to reflux until complete dissolution of solid material occurred, and then concentrated under reduced pressure. The resulting residue was dissolved in water and lyophilized to give the title compound as a beige solid (2.1 g. 100%). 1H NMR (400 MHz, DMSO-d6) δ 0.78-0.96 (m, 6H), 1.21-1.50 (m, 2H), 1.55-1.75 (m, 1H), 1.78-2.07 (m, 3H), 2.10-2.25 (m, 2H). 2.60-2.78 (m, 1H), 2.88-3.15 (m, 2H), 3.65-3.97 (m, 3H), 4.00-4.41 (m, 1H), 5.97 (t, 1H, J=8.0 Hz), 6.21 (d, 1H, J=8.8 Hz), 6.57 (br. s, 2H). 6.95 (d. 1H, J=8.0, 3.2 Hz). MS 395 (MH+-Na).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux until complete dissolution of solid material
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe resulting residue was dissolved in water

Sources & evidence

ORD record
ord-20d5e6f7a00e4e8b8685f0afb0e2d1f7
Source dataset
uspto-grants-2015_09
Patent number
US09138013B2

Reaction notes

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