Triethylamine → HCID 86638017, compound

HRID 881167Notes

Reaction equation

HRID 881167 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5]1[C:6]([C:10]2[N:14]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=3)[C:13](=[O:25])[O:12][N:11]=2)=[N:7][O:8][N:9]=1.[CH3:26][S:27](Cl)(=[O:29])=[O:28].C(N(CC)CC)C>C(OCC)(=O)C>[CH3:26][S:27]([O:1][CH2:2][CH2:3][NH:4][C:5]1[C:6]([C:10]2[N:14]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:22])([F:24])[F:23])[CH:16]=3)[C:13](=[O:25])[O:12][N:11]=2)=[N:7][O:8][N:9]=1)(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66605829HCID 66605829, compound

Product 1

HCID 86638017HCID 86638017, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-{4-[(2-hydroxyethyl)amino]-1,2,5-oxadiazol-3-yl}-4-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5(4H)-one (1.0 g, 2.9 mmol) in ethyl acetate (8.5 mL) was added methanesulfonyl chloride (0.29 mL, 3.7 mmol) in one portion. The reaction was stirred for 5 minutes and triethylamine (0.52 mL, 3.7 mmol) was added, also in one portion. After stirring for an additional 10 minutes, the reaction was quenched with the addition of water (5 mL). The product was extracted with ethyl acetate (2×5 mL), dried over sodium sulfate and concentrated in vacuo to give the desired product (1.2 g, 99%). LCMS calculated for C14H13F3N5O6S (M+H)+: m/z=436.0. 1H NMR (400 MHz, DMSO-d6): δ 8.10 (s, 1H), 7.92 (m, 2H), 7.80 (t, J=8.2 Hz, 1H), 6.77 (t, J=5.9 Hz, 1H), 4.36 (t, J=5.5 Hz, 2H), 3.58 (m, 2H), 3.17 (s, 3H).

Workup

  1. stirringAfter stirring for an additional 10 minutes
  2. customthe reaction was quenched with the addition of water (5 mL)
  3. extractionThe product was extracted with ethyl acetate (2×5 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6cd3a1f15bf346f78d380b5a93670cc4
Source dataset
uspto-grants-2015_03
Patent number
US08993605B2

Reaction notes

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