Triethylamine → HCID 57415394, compound

HRID 333919Notes

Reaction equation

HRID 333919 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]([CH2:7][C:8]2[S:12][C:11]([NH2:13])=[N:10][N:9]=2)=[CH:5][CH:4]=1.CCN(CC)CC.[CH3:23][C:24]1[O:28][C:27]([CH2:29][CH2:30][C:31](Cl)=[O:32])=[CH:26][CH:25]=1>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][C:8]2[S:12][C:11]([NH:13][C:31](=[O:32])[CH2:30][CH2:29][C:27]3[O:28][C:24]([CH3:23])=[CH:25][CH:26]=3)=[N:10][N:9]=2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8002315-(4-methoxybenzyl)-1,3,4-thiadiazol-2-amineHCID 10910039HCID 10910039, compound

Product 1

HCID 57415394HCID 57415394, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 5-(4-methoxybenzyl)-1,3,4-thiadiazol-2-amine (88b, 221 mg, 1.0 mmol), Et3N (0.38 ml) in 1,4-dioxane (8.0 ml) was slowly added 3-(5-methylfuran-2-yl) propanoyl chloride and stirred for further 16.0 hours at room temperature. The reaction mixture was then quenched with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4(s), and concentrated under reduced pressure to give N-[5-(4-methoxy-benzyl)-[1,3,4]thiadiazol-2-yl]-3-(5-methyl-furan-2-yl)-propionamide (88): 1H NMR (500 MHz, DMSO) δ7.24(d, 2H), δ6.89(d, 2H), δ5.90(d, 2H), δ4.24(s, 2H), δ3.72(s, 3H), δ2.83 (d, 3H), δ2.71(d, 2H), δ2.17(s, 3H). ESI-MS: 358.0 (M+H)+.

Workup

  1. customThe reaction mixture was then quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4(s)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-17f3ddabef614e49bf8e15c853d1edc0
Source dataset
uspto-grants-2014_11
Patent number
US08883793B2

Reaction notes

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