3-Butenoic acid → HCID 46916454, compound

HRID 2045932Notes

Reaction equation

HRID 2045932 reaction equation
[CH:1]([CH2:3][C:4]([OH:6])=O)=[CH2:2].C(Cl)(=O)C(Cl)=O.[N:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[CH:15][C:14]=1[C:23]1[CH:24]=[C:25]([NH2:29])[CH:26]=[CH:27][CH:28]=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl.C1COCC1.C(OCC)(=O)C.CN(C=O)C>[N:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[CH:15][C:14]=1[C:23]1[CH:24]=[C:25]([NH:29][C:4](=[O:6])[CH2:3][CH:1]=[CH2:2])[CH:26]=[CH:27][CH:28]=1

Participants

9

Reactant 4

HCID 327433-Butenoic acidHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 8072643-(2-quinoxalinyl)aniline

Product 1

HCID 46916454HCID 46916454, compoundYield 26.8%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of vinylacetic acid (43 μL, 0.497 mmol) and oxalyl chloride (48 μL, 0.542 mmol) in DCM (5 mL), a drop of DMF was added using a Pasteur pipette. The colourless solution was stirred at room temperature for 15 min, and a solution of (3-quinoxalin-2-ylphenyl)amine (100 mg, 0.452 mmol) and diisopropylethylamine (DIEA, 90 μL, 0.542 mmol) in THF (5 mL) was added. The resulting slurry was stirred at room temperature for 24 hrs, the reaction mixture was then diluted with ethyl acetate (30 mL) and washed with water (2×25 mL), the organic phase dried over sodium sulphate and the solvent evaporated in vacuo. The resulting crude solid was purified by preparative LCMS to afford N-(3-(quinoxalin-2-yl)phenyl)but-3-enamide (35 mg, 22% yield). LCMS calculated for C18H15N3O (M+H): 290.33. found 290.24. 1H-NMR (DMSO-d6, 400 Mhz) δH: 10.59 (1H, br.), 9.52 (1H, s), 8.52 (1H, m), 8.12-8.16 (2H, m), 8.05-8.08 (1H, m), 7.80-7.95 (3H, m), 7.55-7.60 (1H, m), 5.95-6.07 (1H, m), 5.25-5.12 (2H, m), 3.18 (2H, d, J=6.2 Hz).

Workup

  1. stirringThe resulting slurry was stirred at room temperature for 24 hrs
  2. washwashed with water (2×25 mL)
  3. dry with materialthe organic phase dried over sodium sulphate
  4. customthe solvent evaporated in vacuo
  5. customThe resulting crude solid was purified by preparative LCMS

Sources & evidence

ORD record
ord-516b483d2bda4c96b872c53dcec40b3d
Source dataset
uspto-grants-2013_11
Patent number
US08592415B2

Reaction notes

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