Hydrochloric Acid → HCID 86730123, compound

HRID 1467360Notes

Reaction equation

HRID 1467360 reaction equation
[NH2:1][C:2]1[C:3]2[C:13]([O:14][CH2:15][C:16]([NH:19]C(=O)[O-])([CH3:18])[CH3:17])=[CH:12][CH:11]=[CH:10][C:4]=2[NH:5][S:6](=[O:9])(=[O:8])[N:7]=1.[ClH:23]>C(O)C>[Cl-:23].[NH2:1][C:2]1[C:3]2[C:13]([O:14][CH2:15][C:16]([CH3:18])([NH3+:19])[CH3:17])=[CH:12][CH:11]=[CH:10][C:4]=2[NH:5][S:6](=[O:9])(=[O:8])[N:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86730125HCID 86730125, compound

Product 1

HCID 86730123HCID 86730123, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl(1-((4-amino-2,2-dioxido-1H-benzo[c][1,2,6]thiadiazin-5-yl)oxy)-2-methylpropan-2-yl-carbamate (114 g, 296 mmol) in ethanol (1 L), cooled to 0° C., was added HCl (4.0 M in dioxane, 370 mL, 1480 mmol). The mixture was stirred at 0° C. for 3 hours under nitrogen, and then allowed to warm to room temperature. The mixture was concentrated and the residue was suspended in diethyl ether (2 L) and refluxed for 1 hour. The mixture was cooled to room temperature and the solid was collected by vacuum filtration and dried under high vacuum to afford 1-((4-amino-2,2-dioxido-1H-benzo[c][1,2,6]thiadiazin-5-yl)oxy)-2-methylpropan-2-aminium chloride as a white solid (94 g, 100%). 1H NMR (DMSO-d6), 400 MHz: δ 1.37 (s, 6H), 4.12 (s, 2H), 6.70 (d, J=8.0 Hz, 1H), 6.85 (d, J=8.0 Hz, 1H), 7.48 (t, J=8.0 Hz, 1H), 7.65 (s, 1H), 8.43 (br s, 3H), 10.9 (br s, 1H). MS 285 (MH+).

Workup

  1. temperatureto warm to room temperature
  2. concentrationThe mixture was concentrated
  3. temperaturerefluxed for 1 hour
  4. temperatureThe mixture was cooled to room temperature
  5. filtrationthe solid was collected by vacuum filtration
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-34c9c2d1b47943108773d1504fdf8d0b
Source dataset
uspto-grants-2015_04
Patent number
US09000151B2

Reaction notes

Loading…