2-Chlorobenzoyl chloride → N-[5-(5-chloro-2-methylbenzoxazol-6-yl)(2-pyridyl)](2-chlorophenyl)carboxamide

HRID 2272180Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2272180
[Cl:1][C:2]1[C:3]([C:12]2[CH:13]=[CH:14][C:15]([NH2:18])=[N:16][CH:17]=2)=[CH:4][C:5]2[O:9][C:8]([CH3:10])=[N:7][C:6]=2[CH:11]=1.[Cl:19][C:20]1[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=1[C:22](Cl)=[O:23].CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+].C(Cl)Cl>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Cl:1][C:2]1[C:3]([C:12]2[CH:13]=[CH:14][C:15]([NH:18][C:22]([C:21]3[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=3[Cl:19])=[O:23])=[N:16][CH:17]=2)=[CH:4][C:5]2[O:9][C:8]([CH3:10])=[N:7][C:6]=2[CH:11]=1

Komponenten

7

Edukt 4

HCID 691102-Chlorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 23716255Sodium bicarbonate methylene chlorideHCID 584870245-(5-Chloro-2-methylbenzoxazol-6-yl)-2-pyridylamine

Produkt 1

HCID 58486904N-[5-(5-chloro-2-methylbenzoxazol-6-yl)(2-pyridyl)](2-chlorophenyl)carboxamideAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 5-(5-chlorob-2-methylenzoxazol-6-yl)-2-pyridylamine (36) (19 mg, 0.073 mmol) and 2 mg DMAP in 2 ml DCM was added 2-chlorobenzoyl chloride (19 μl, 0.14 mmol) followed by addition of DIEA (64 μl). The resulting solution was stirred at r.t. for overnight. The reaction mixture was worked up with aq. NaHCO3/DCM. DCM phase was washed with brine, concentrated to dryness. The residue was dissolved in 2 ml THF/MeOH/H2O (5:4:1) and stirred with 1N NaOH (140 μl) at r.t. for 1 h before worked up with EA/aq. NaHCO3. Silica gel flash chromatography furnished 20.6 mg 37 as pale yellow solid. (yield: 71%).

Aufarbeitung

  1. washDCM phase was washed with brine
  2. concentrationconcentrated to dryness
  3. dissolutionThe residue was dissolved in 2 ml THF/MeOH/H2O (5:4:1)
  4. stirringstirred with 1N NaOH (140 μl) at r.t. for 1 h

Quellen und Nachweise

ORD-Eintrag
ord-c5dfafc5647a4fe6869accfec769f17c
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09120751B2

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