Diisopropylethylamine → 2-chloro-N-(3-(quinoxalin-2-yl)phenyl)propanamide

HRID 2045930Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2045930
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[C:11]1[CH:12]=[C:13]([NH2:17])[CH:14]=[CH:15][CH:16]=1.C(N(C(C)C)CC)(C)C.[Cl:27][CH:28]([CH3:32])[C:29](Cl)=[O:30]>C1COCC1.C(OCC)(=O)C>[Cl:27][CH:28]([CH3:32])[C:29]([NH:17][C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([C:2]2[CH:3]=[N:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=2)[CH:12]=1)=[O:30]

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 1110192-Chloropropionyl chlorideHCID 8072643-(2-Quinoxalinyl)aniline

Produkt 1

HCID 582003822-chloro-N-(3-(quinoxalin-2-yl)phenyl)propanamideAusbeute 52,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of (3-quinoxalin-2-ylphenyl)amine (124 mg, 0.560 mmol) and diisopropylethylamine (DIEA, 111 μL, 0.672 mmol) in THF (5 mL), 2-chloropropionyl chloride (60 μL, 0.620 mmol) was added at room temperature. The reaction mixture was stirred at room temperature for 24 hrs and then diluted with ethyl acetate (20 mL). The organic phase was washed with water (20 mL), dried over MgSO4 and the solvent was evaporated in vacuo to afford 2-chloro-N-(3-(quinoxalin-2-yl)phenyl)propanamide (92 mg, 52% yield). LCMS calculated for C17H14ClN3O (M+H): 312.77. found 313. 1H-NMR (DMSO-d6, 400 Mhz) δH: 10.52 (1H, br.), 9.53 (1H, s), 8.55 m), 8.12-8.18 (2H, m), 8.05-8.08 (1H, m), 7.82-7.95 (3H, m), 7.55-7.60 (1H, m), 4.75 (1H, q, J=6.8 Hz), 1.68 (3H, d, J=6.8 Hz).

Aufarbeitung

  1. washThe organic phase was washed with water (20 mL)
  2. dry with materialdried over MgSO4
  3. customthe solvent was evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b4c9fd160ff64e519349a304e6476626
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08592415B2

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