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 333007Notes

Reaction equation

HRID 333007 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-8d9ba0e802374b1e83126d738e108da5
Source dataset
uspto-grants-2014_11
Patent number
US08877922B2

Reaction notes

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