2-Fluorobenzoyl chloride → N-benzyl-2-(2-fluorobenzamido)isonicotinamide

HRID 714317Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 714317
[NH2:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][N:17]=1)[C:5]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].[F:18][C:19]1[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21](Cl)=[O:22]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1.ClCCl>[CH2:8]([NH:7][C:5](=[O:6])[C:4]1[CH:15]=[CH:16][N:17]=[C:2]([NH:1][C:21](=[O:22])[C:20]2[CH:24]=[CH:25][CH:26]=[CH:27][C:19]=2[F:18])[CH:3]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Komponenten

6

Edukt 2

HCID 98082-Fluorobenzoyl chlorideHCID 187528972-amino-N-benzylisonicotinamide

Produkt 1

HCID 67153822N-benzyl-2-(2-fluorobenzamido)isonicotinamideAusbeute 45,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-amino-N-benzylisonicotinamide (0.10 g, 0.44 mmol) and 4-dimethylaminopyridine (0.01 g, 0.08 mmol) in pyridine (3.0 mL) was added 2-fluorobenzoyl chloride (0.07 g, 0.44 mmol). The resulting solution was stirred at ambient temperature for 16 hours, diluted with dichloromethane (25 mL), washed with water (2×25 mL) and brine (10 mL). The organic solution was dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluting with 45% ethyl acetate in hexanes to give N-benzyl-2-(2-fluorobenzamido)isonicotinamide as a colorless solid (0.07 g, 44%): mp 175-176° C. (hexanes/ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 9.21 (d, J=13.7 Hz, 1H), 8.64 (s, 1H), 8.46-8.42 (m, 1H), 8.12-8.06 (m, 1H), 7.64-7.48 (m, 2H), 7.35-7.16 (m, 7H), 6.68 (s, 1H), 4.65 (d, J=5.7 Hz, 2H); 13C NMR (CDCl3, 75 MHz) δ 165.2, 162.1, 161.9, 158.8, 151.7, 148.8, 144.1, 137.5, 134.5, 134.4, 131.9, 128.8, 127.7, 125.1, 120.7, 118.8, 116.6, 116.3, 111.0, 44.2; MS (ES+) m/z 350.6 (M+1).

Aufarbeitung

  1. washwashed with water (2×25 mL) and brine (10 mL)
  2. dry with materialThe organic solution was dried over anhydrous sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography
  6. washeluting with 45% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-aac1288bc26d41f98a1d833708095822
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187426B2

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