Sodium;3-oxidodioxaborirane;tetrahydrate → HCID 66613909, compound

HRID 1404701Notes

Reaction equation

HRID 1404701 reaction equation
B1([O-])OO1.[OH2:5].O.O.O.[Na+].[CH3:10][N:11]([C:18]1[S:19][C:20]([C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)=[N:21][N:22]=1)[C:12](=[O:17])[CH2:13][CH2:14][S:15][CH3:16]>C(O)(=O)C.C(=O)(O)[O-].[Na+]>[CH3:10][N:11]([C:18]1[S:19][C:20]([C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)=[N:21][N:22]=1)[C:12](=[O:17])[CH2:13][CH2:14][S:15]([CH3:16])=[O:5]

Participants

5

Reactant 2

HCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrateHCID 66613348HCID 66613348, compound

Product 1

HCID 66613909HCID 66613909, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
23 °C

Procedure

Sodium perborate tetrahydrate (52 mg, 0.34 mmol, 1.0 equiv) was added to a stirred solution of N-methyl-3-(methylthio)-N-(5-(pyridin-3-yl)-1,3,4-thiadiazol-2-yl)propanamide (100 mg, 0.34 mmol, 1.0 equiv) in glacial acetic acid (1.8 mL) at 23° C. The resulting suspension was stirred at 23° C. for 3 h. The reaction mixture was diluted with a saturated solution of sodium bicarbonate (50 mL) and extracted with dichloromethane (5×20 mL). The combined organic layers were dried (Na2SO4), gravity-filtered, and concentrated by rotary evaporation. The residue was rinsed with cold ethyl acetate and vacuum-filtered to afford the title compound as an off-white powder (82 mg, 78% yield): mp 138-140° C.; 1H NMR (300 MHz, DMSO-d6) δ 9.12 (d, J=2 Hz, 1H), 8.71 (dd, J=5, 2 Hz, 1H), 8.34 (m, 1H), 7.56 (dd, J=8, 5 Hz, 1H), 3.80 (s, 3H), 2.90-3.30 (m, 3H), 2.62 (s, 3H); ESIMS m/z 311 ([M+H]+). Compounds 32, 45, 51, and 77 were prepared as described in Example 10.

Workup

  1. extractionextracted with dichloromethane (5×20 mL)
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. filtrationgravity-filtered
  4. concentrationconcentrated by rotary evaporation
  5. washThe residue was rinsed with cold ethyl acetate
  6. filtrationvacuum-filtered

Sources & evidence

ORD record
ord-29ec75c57d33446583fa4968e45eb732
Source dataset
uspto-grants-2014_12
Patent number
US08912338B2

Reaction notes

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