Sodium;3-oxidodioxaborirane;tetrahydrate → HCID 66612604, compound

HRID 1911963Notes

Reaction equation

HRID 1911963 reaction equation
B1([O-])OO1.[OH2:5].[OH2:6].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:6])=[O:5]

Participants

5

Reactant 2

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

Product 1

HCID 66612604HCID 66612604, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
60 °C

Procedure

Sodium perborate tetrahydrate (130 mg, 0.84 mmol, 2.4 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 yellow suspension was heated to 60° C. for 15 h. The cooled reaction mixture was diluted with a saturated solution of sodium bicarbonate (50 mL) and extracted with dichloromethane (3×30 mL). The combined organic layers were dried (sodium sulfate), 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 (90 mg, 82% yield): mp 199-201° C.; 1H NMR (300 MHz, DMSO-d6) δ 9.15 (d, J=2 Hz, 1H), 8.73 (dd, J=6, 2 Hz, 1H), 8.32 (dt, J=8, 2 Hz, 1H), 7.46 (dd, J=8, 5 Hz, 1H), 3.94 (s, 3H), 3.59 (t, J=7 Hz, 2H), 3.33 (t, J=7 Hz, 2H), 3.09 (s, 3H); ESIMS m/z 327 ([M+H]+).

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted with dichloromethane (3×30 mL)
  3. dry with materialThe combined organic layers were dried (sodium sulfate), gravity
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation
  6. washThe residue was rinsed with cold ethyl acetate
  7. filtrationvacuum-filtered

Sources & evidence

ORD record
ord-ace2c55bbfde41648ce914c4fa987950
Source dataset
uspto-grants-2013_12
Patent number
US08604211B2

Reaction notes

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