Hydrochloric Acid → HCID 85469555, compound

HRID 1467363Notes

Reaction equation

HRID 1467363 reaction equation
[NH2:1][C:2]1[C:3]2[C:13]([O:14][CH2:15][C:16]([NH:19][C:20](=[O:29])[C:21]3[CH:26]=[CH:25][N:24]=[C:23]([C:27]#[N:28])[CH:22]=3)([CH3:18])[CH3:17])=[CH:12][CH:11]=[CH:10][C:4]=2[NH:5][S:6](=[O:9])(=[O:8])[N:7]=1.[OH-:30].[Na+].Cl>C(O)C.O>[NH2:1][C:2]1[C:3]2[C:13]([O:14][CH2:15][C:16]([NH:19][C:20]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([C:27]([NH2:28])=[O:30])[CH:22]=3)=[O:29])([CH3:18])[CH3:17])=[CH:12][CH:11]=[CH:10][C:4]=2[NH:5][S:6](=[O:9])(=[O:8])[N:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 85468994HCID 85468994, compound

Product 1

HCID 85469555HCID 85469555, compoundYield 30.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-(1-((4-amino-2,2-dioxido-1H-benzo[c][1,2,6]thiadiazin-5-yl)oxy)-2-methylpropan-2-yl)-2-cyanoisonicotinamide (300 mg, 724 umol) in ethanol (20 mL) at room temperature, was added a solution of sodium hydroxide (275 mg, 7.06 mmol) in water (6 mL). The reaction was microwaved at 80° C. for five minutes, and upon completion was cooled 0° C., neutralized with 1N HCl, concentrated and purified by flash chromatography (1/9 methanol/dichloromethane). The purified product was washed with hot ethanol and the solid was collected by vacuum filtration and dried under vacuum at 50° C. to yield N4-(1-((4-amino-2,2-dioxido-1H-benzo[c][1,2,6]thiadiazin-5-yl)oxy)-2-methylpropan-2-yl)pyridine-2,4-dicarboxamide (95 mg, 29%) as a white solid. 1H NMR (DMSO-d6, 400 MHz): δ 1.50 (s, 6 H), 4.38 (s, 2H), 6.62 (d, J=0.8 Hz, 1H), 6.80 (d, J=8.4 Hz, 1 H), 7.47 (t, J=8.4 Hz, 1H), 7.75 (s, 1H), 7.80 (s, 1H), 7.86 (dd, J=5.2 Hz, 1H), 8.19 (s, 1H), 8.35 (s, 1H), 8.39 (s, 1H), 8.69 (s, 1H), 8.73 (dd, J=4.8 Hz, 1H), 10.99 (s, 1H). MS 433 (MH+).

Workup

  1. customThe reaction was microwaved at 80° C. for five minutes
  2. concentrationconcentrated
  3. custompurified by flash chromatography (1/9 methanol/dichloromethane)
  4. washThe purified product was washed with hot ethanol
  5. filtrationthe solid was collected by vacuum filtration
  6. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-e6cad3ee08f249dd85c5d9494f8a1510
Source dataset
uspto-grants-2015_04
Patent number
US09000151B2

Reaction notes

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