Triethylamine → 2-[(4-{4-[(4-Bromo-2-furyl)methyl]-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl}-1,2,5-oxadiazol-3-yl)amino]ethyl methanesulfonate

HRID 2402247Notes

Reaction equation

HRID 2402247 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:7][N:8]2[C:12](=[O:13])[O:11][N:10]=[C:9]2[C:14]2[C:18]([NH:19][CH2:20][CH2:21][OH:22])=[N:17][O:16][N:15]=2)[O:5][CH:6]=1.[CH3:23][S:24](Cl)(=[O:26])=[O:25].C(N(CC)CC)C>C(OCC)(=O)C>[CH3:23][S:24]([O:22][CH2:21][CH2:20][NH:19][C:18]1[C:14]([C:9]2[N:8]([CH2:7][C:4]3[O:5][CH:6]=[C:2]([Br:1])[CH:3]=3)[C:12](=[O:13])[O:11][N:10]=2)=[N:15][O:16][N:17]=1)(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 666059514-[(4-Bromo-2-furyl)methyl]-3-{4-[(2-hydroxyethyl)amino]-1,2,5-oxadiazol-3-yl}-1,2,4-oxadiazol-5(4H)-one

Product 1

HCID 866380282-[(4-{4-[(4-Bromo-2-furyl)methyl]-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl}-1,2,5-oxadiazol-3-yl)amino]ethyl methanesulfonateYield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-[(4-bromo-2-furyl)methyl]-3-{4-[(2-hydroxyethyl)amino]-1,2,5-oxadiazol-3-yl}-1,2,4-oxadiazol-5(4H)-one (7.7 g, 21 mmol, containing also some of the corresponding bromo-compound) in ethyl acetate (100 mL) was added methanesulfonyl chloride (0.96 mL, 12 mmol) in one portion. The reaction was stirred for 5 minutes and triethylamine (1.6 mL, 11 mmol) was added, also in one portion. After stirring for 30 minutes, additional methanesulfonyl chloride (0.4 mL, 5 mmol) was added, followed 5 minutes later by triethylamine (0.58 mL, 4.2 mmol). After 15 minutes, the reaction was quenched with the addition of water (100 mL). The product was extracted with ethyl acetate (3×50 mL) and the combined organic layers washed with brine (100 mL). After drying over sodium sulfate, the solvent was removed in vacuo to give the desired product (9.3 g, 100%). LCMS calculated for C12H13BrN5O7S (M+H)+: m/z=449.8, 451.8. 1H NMR (300 MHz, DMSO-d6): δ 7.88 (s, 1H), 6.73 (t, J=6.2 Hz, 1H), 6.68 (s, 1H), 5.08 (s, 2H), 4.37 (m, 2H), 3.59 (q, J=5.8 Hz, 2H), 3.16 (s, 3H).

Workup

  1. stirringAfter stirring for 30 minutes
  2. waitAfter 15 minutes
  3. customthe reaction was quenched with the addition of water (100 mL)
  4. extractionThe product was extracted with ethyl acetate (3×50 mL)
  5. washthe combined organic layers washed with brine (100 mL)
  6. dry with materialAfter drying over sodium sulfate
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-3b115408b1764aa3a0010fae7c5aef61
Source dataset
uspto-grants-2014_08
Patent number
US08796319B2

Reaction notes

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