Acetic Acid → HCID 67399989, compound

HRID 711913Notes

Reaction equation

HRID 711913 reaction equation
O1CCCCC1[O:7][CH2:8][CH2:9]/[CH:10]=[CH:11]/[C:12]1[C:21]2[C:20]([NH2:22])=[N:19][S:18](=[O:24])(=[O:23])[NH:17][C:16]=2[CH:15]=[CH:14][CH:13]=1.CC(O)=O.O>C1COCC1>[NH2:22][C:20]1[C:21]2[C:12](/[CH:11]=[CH:10]/[CH2:9][CH2:8][OH:7])=[CH:13][CH:14]=[CH:15][C:16]=2[NH:17][S:18](=[O:24])(=[O:23])[N:19]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 67399748HCID 67399748, compound

Product 1

HCID 67399989HCID 67399989, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of (E)-5-(4-(tetrahydro-2H-pyran-2-yloxy)but-1-enyl)-1H-benzo[c][1,2,6]thiadiazin-4-amine-2,2-dioxide (322 mmol, 43 mg) (Example 273) in THF (860 μL) was added AcOH (1.7 mL) and water (430 μL) and the solution heated overnight at 45° C. The solution was cooled to room temperature and the solvent evaporated. The residue was triturated with boiling water then cooled to room temperature. The resulting solid was collected and washed with water to give the desired product (69 mg, 80%) as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 2.365 (q, J=6 Hz, 2H), 3.568 (q, J=6 Hz, 2H), 4.681 (t, J=6 Hz, 1H), 6.186 (d of t, J=7 Hz, 16 Hz, 1H), 6.786 (d, J=16 Hz, 1H), 6.922 (d, J=8 Hz, 1H), 7.022 (br. s, 1H), 7.088 (d, J=8 Hz, 1H), 7.468 (t, J=8 Hz, 1H), 8.388 (br. s, 1H), 10.935 (s, 1H). MS 268 (MH+).

Workup

  1. temperatureThe solution was cooled to room temperature
  2. customthe solvent evaporated
  3. customThe residue was triturated with boiling water
  4. temperaturethen cooled to room temperature
  5. customThe resulting solid was collected
  6. washwashed with water

Sources & evidence

ORD record
ord-82ffe19bc1554c4980376ee41af6d7a7
Source dataset
uspto-grants-2015_11
Patent number
US09181276B2

Reaction notes

Loading…