4-Methylmorpholine → HCID 24738248, Verbindung

HRID 19808Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 19808
[Cl:1][C:2]1[C:3]([F:15])=[C:4]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:5]([OH:7])=O.[C:16]([C:20]1[CH:36]=[CH:35][C:23]([CH2:24][NH:25][CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=2)=[CH:22][CH:21]=1)([CH3:19])([CH3:18])[CH3:17].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>CN(C=O)C.[Cl-].[Na+].O.O>[C:16]([C:20]1[CH:36]=[CH:35][C:23]([CH2:24][N:25]([CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=2)[C:5](=[O:7])[C:4]2[CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=[C:2]([Cl:1])[C:3]=2[F:15])=[CH:22][CH:21]=1)([CH3:19])([CH3:17])[CH3:18]

Komponenten

8

Edukt 4

HCID 79724-MethylmorpholineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27737513-Chloro-2-fluoro-5-(trifluoromethyl)benzoic acidHCID 29792506(4-Tert-butylbenzyl)-[2-(4-chlorophenyl)-ethyl]-amine

Produkt 1

HCID 24738248HCID 24738248, VerbindungAusbeute 70,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To a solution of 50 mg of 3-chloro-2-fluoro-5-trifluoromethyl-benzoic acid (0.206 mmol) and 68 mg (0.225 mmol) of (4-tert-butylbenzyl)-[2-(4-chlorophenyl)-ethyl]-amine in 3 ml of DMF were added 117 mg of HBTU (0.31 mmol) and 0.063 ml (0.62 mmol) of 4-methylmorpholine. After stirring the reaction mixture over night at RT it was poured on a mixture of 15 ml of brine and 15 ml of water and extracted with ethyl acetate. The combined organic phases were washed with brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (silica gel; heptane/EtOAc 95:5) to give 76 mg (70%) of a light yellow amorphous material. MS (ISP) 526.0 (M+H)+. In analogy to example 1:

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (silica gel; heptane/EtOAc 95:5)

Quellen und Nachweise

ORD-Eintrag
ord-6882ab2e821742b9ba6189db1000c720
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745477B2

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