4-Methylmorpholine → N-[5-(5-chloro-2-methylbenzoxazol-6-yl)phenyl](3-fluoro(4-pyridyl))carboxamide

HRID 407107

Reaktionsgleichung

Reaktionsgleichung von HRID 407107
[F:1][C:2]1[CH:10]=[N:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.ClC1N=C(OC)N=C(OC)[N:13]=1.CN1CCOCC1.[Cl:29][C:30]1[C:31]([C:40]2[CH:45]=[CH:44][C:43](N)=[CH:42][CH:41]=2)=[CH:32][C:33]2[O:37][C:36]([CH3:38])=[N:35][C:34]=2[CH:39]=1.C([O-])(O)=O.[Na+].CC(=O)OCC>C(Cl)Cl>[Cl:29][C:30]1[C:31]([C:40]2[CH:45]=[CH:44][CH:43]=[C:42]([NH:13][C:4]([C:3]3[CH:7]=[CH:8][N:9]=[CH:10][C:2]=3[F:1])=[O:6])[CH:41]=2)=[CH:32][C:33]2[O:37][C:36]([CH3:38])=[N:35][C:34]=2[CH:39]=1

Komponenten

7

Edukt 5

HCID 79724-MethylmorpholineHCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazineHCID 3453613-Fluoropyridine-4-carboxylic acidHCID 674672954-(5-Chloro-2-methylbenzoxazol-6-yl)phenylamineHCID 86584982Sodium bicarbonate ethyl acetate

Produkt 1

HCID 67468423N-[5-(5-chloro-2-methylbenzoxazol-6-yl)phenyl](3-fluoro(4-pyridyl))carboxamideAusbeute 95,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A suspension of 3-fluoroisonicotinic acid (20 mg, 0.14 mmol), 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) (28 mg, 0.16 mmol) and 40 μl N-methyl morpholine in 1 ml DCM was stirred at r.t. for 1 h before addition of 56 (20 mg, 0.078 mmol). The resulting reaction mixture was stirred at r.t. for overnight. The reaction mixture was worked up with aq. NaHCO3/EA. Org. phase was washed with brine, concentrated, subjected to silica flash column chromatography to furnish 28.5 mg title compound 60 as off-white solid. (Yield: 95.7%).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. washphase was washed with brine
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-88aed97be0df4e2c8b6be259ac849e52
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754219B2

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