3-(Trifluoromethyl)aniline → HCID 12135271, Verbindung

HRID 858939Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 858939
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:12]=[C:11]([CH2:13][NH:14][C:15]2[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=2[C:17]([OH:19])=O)[CH:10]=[CH:9][N:8]=1.[NH2:24][C:25]1[CH:26]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:29][CH:30]=1.CN1CCOCC1>CN(C)C=O.C(OCC)(=O)C>[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:12]=[C:11]([CH2:13][NH:14][C:15]2[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=2[C:17]([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:32])([F:33])[F:34])[CH:26]=2)=[O:19])[CH:10]=[CH:9][N:8]=1

Komponenten

6

Edukt 3

HCID 73753-(Trifluoromethyl)anilineHCID 79724-MethylmorpholineHCID 587636722-{[2-(2-Oxo-pyrrolidin-1-yl)-pyridin-4-ylmethyl]-amino}-benzoic Acid

Produkt 1

HCID 12135271HCID 12135271, VerbindungAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

156 mg (0.5 mmol) of 2-{[2-(2-oxo-pyrrolidin-1-yl)-pyridin-4-ylmethyl]-amino}-benzoic acid is mixed in 5 ml of dimethylformamide with 0.12 ml (1 mmol) of 3-aminobenzotrifluoride, 228 mg (0.6 mmol) of HATU (N-dimethylamino-1H-1,2,3-triazolo-[4,5-b]pyridin-1-ylmethylene]-N-methylmethanammoniumhexafluorophosphate-N-oxide) and 0.14 ml of N-methylmorpholine, and it is stirred overnight at room temperature. It is diluted with ethyl acetate and washed in succession with saturated sodium bicarbonate solution, water and saturated common salt solution. The organic phase is dried, filtered and concentrated by evaporation. The residue is chromatographed on Isolute as a mobile solvent. 95 mg (42% of theory) of 2-{[2-(2-oxo-pyrrolidin-1-yl)-pyridin-4-ylmethyl]-amino}-N-(3-trifluoromethyl-phenyl)-benzamide is obtained.

Aufarbeitung

  1. washwashed in succession with saturated sodium bicarbonate solution, water and saturated common salt solution
  2. customThe organic phase is dried
  3. filtrationfiltered
  4. concentrationconcentrated by evaporation
  5. customThe residue is chromatographed on Isolute as a mobile solvent

Quellen und Nachweise

ORD-Eintrag
ord-9da4042584f442019de6f247fc7f3675
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07148357B2

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