Triethylamine → HCID 67434957, compound

HRID 1662991Notes

Reaction equation

HRID 1662991 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH:18]=[N:17][CH:16]=[N:15]2)=[CH:10][CH:9]=1)[CH3:2].[CH2:20]([O:24][C:25]1[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1)[CH2:21][CH:22]=[CH2:23].C(N(CC)CC)C>O1CCOCC1.O>[CH2:1]([O:3][C:4](=[O:19])[CH2:5][N:6]([S:31]([C:28]1[CH:27]=[CH:26][C:25]([O:24][CH2:20][CH2:21][CH:22]=[CH2:23])=[CH:30][CH:29]=1)(=[O:33])=[O:32])[CH2:7][C:8]1[CH:9]=[CH:10][C:11]([N:14]2[CH:18]=[N:17][CH:16]=[N:15]2)=[CH:12][CH:13]=1)[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 21884792HCID 21884792, compoundHCID 67434472HCID 67434472, compound

Product 1

HCID 67434957HCID 67434957, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2 g (7.683 mmol) of (4-[1,2,4]triazol-1-yl-benzylamino)-acetic acid ethyl ester in 15 ml of dioxane and 15 ml of H2O, 2.3 g (9.22 mmol) of 4-but-3-enyloxy-benzenesulfonyl chloride and 1.3 ml (9.22 mmol) of triethyl amine are successively added at 0-5° C. After being stirred for 18 h at r.t., the reaction mixture is diluted with H2O and extracted with AcOEt. The combined extracts are washed with brine, dried over MgSO4 and concentrated under reduced pressure. The residue is purified by column chromatography on silica gel to give the title compound. 1H-NMR (400 MHz, CDCl3): 1.17 (t, 3H, J=7.04 Hz), 2.55-2.65 (m, 2H), 3.95 (s, 2H), 4.07 (t, 2H, J=7.04 Hz), 4.09 (t, 2H, J=6.56 Hz), 4.53 (s, 2H), 5.10-5.25 (m, 2H), 5.85-5.95 (m, 1H), 6.99 (d, 2H, J=8.04 Hz), 7.44 (d, 2H, J=7.56 Hz), 7.64 (d, 2H, J=8.04 Hz), 7.82 (d, 2H, J=7.56 Hz), 8.11 (s, 1H), 8.55 (s, 1H).

Workup

  1. extractionextracted with AcOEt
  2. washThe combined extracts are washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-87af44e879034708b81da6608dd215e5
Source dataset
uspto-grants-2011_10
Patent number
US08034810B2

Reaction notes

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