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4-Methylmorpholine → 2-amino-5-chloro-N-(4-cyclopropyl-benzyl)-N-[2-(3-trifluoromethyl-phenyl)-ethyl]-benzamide

HRID 2244380
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2244380
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH:12]1([C:15]2[CH:34]=[CH:33][C:18]([CH2:19][NH:20][CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=3)=[CH:17][CH:16]=2)[CH2:14][CH2:13]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>CN(C=O)C.O>[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([N:20]([CH2:19][C:18]1[CH:17]=[CH:16][C:15]([CH:12]2[CH2:14][CH2:13]2)=[CH:34][CH:33]=1)[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:30])([F:31])[F:32])[CH:24]=1)=[O:6]
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Komponenten

7

Edukt 4

HCID 79724-MethylmorpholineHCID 124762-Amino-5-chlorobenzoic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68695622(4-Cyclopropyl-benzyl)-[2-(3-trifluoromethyl-phenyl)-ethyl]-amine

Produkt 1

HCID 68699048
2-amino-5-chloro-N-(4-cyclopropyl-benzyl)-N-[2-(3-trifluoromethyl-phenyl)-ethyl]-benzamide
Ausbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 53 mg of 2-amino-5-chloro-benzoic acid (0.33 mmol) and 105 mg (0.33 mmol) of (4-cyclopropyl-benzyl)-[2-(3-trifluoromethyl-phenyl)-ethyl]-amine in 4.5 ml of DMF were added 171 mg of HBTU (0.45 mmol) and 0.1 ml (0.9 mmol) of 4-methyl-morpholine. After stirring the reaction mixture over night at RT it was diluted with 50 ml water and extracted with ethyl acetate. The combined organic phases were washed with 10% aqueous KHCO3 solution, 0.1M HCl solution and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The remaining oil was purified by column chromatography (silica gel; heptane/EtOAc 6:1) to give 127 mg (88%) of 2-amino-5-chloro-N-(4-cyclopropyl-benzyl)-N-[2-(3-trifluoromethyl-phenyl)-ethyl]-benzamide as a yellow oil. MS (ISP) 473 (M+H)+.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe combined organic phases were washed with 10% aqueous KHCO3 solution, 0.1M HCl solution and brine
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe remaining oil was purified by column chromatography (silica gel; heptane/EtOAc 6:1)

Quellen und Nachweise

ORD-Eintrag
ord-177e17c91932466a8801c4a8940e06fa
Quelldatensatz
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07678818B2

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