4-Methylmorpholine → HCID 86603052, Verbindung

HRID 855348

Reaktionsgleichung

Reaktionsgleichung von HRID 855348
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([OH:13])=O)[CH:10]=1)[NH:7][CH:6]=[CH:5]2.[C:14]([C:18]1[CH:37]=[CH:36][C:21]([CH2:22][NH:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=2)=[CH:20][CH:19]=1)([CH3:17])([CH3:16])[CH3:15].CN1CCOCC1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C.O>[C:14]([C:18]1[CH:37]=[CH:36][C:21]([CH2:22][N:23]([CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:33])[F:34])[CH:27]=2)[C:11]([C:9]2[CH:10]=[C:2]([Br:1])[CH:3]=[C:4]3[C:8]=2[NH:7][CH:6]=[CH:5]3)=[O:13])=[CH:20][CH:19]=1)([CH3:17])([CH3:15])[CH3:16]

Komponenten

7

Edukt 4

HCID 79724-MethylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 533992575-Bromo-1H-indole-7-carboxylic acidHCID 68560440(4-Tert-butyl-benzyl)-[2-(3-trifluoromethyl-phenyl)-ethyl]-amine

Produkt 1

HCID 86603052HCID 86603052, VerbindungAusbeute 90,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 80 mg (0.3 mmol) 5-bromo-1H-indole-7-carboxylic acid and 112 mg (0.33 mmol) (4-tert-butyl-benzyl)-[2-(3-trifluoromethyl-phenyl)-ethyl]-amine in 3 ml DMF, were added 0.1 ml (0.91 mmol) of N-methylmorpholine and 173 mg of TBTU (0.45 mmol) at rt. After stirring for 17 h at rt, the reaction mixture was diluted with 33 ml water and extracted with EtOAc (2×). The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (8 g silica gel; DCM/heptane 50:50 to 70:30) to give 152 mg white powder (90%). MS (ISP) 574.3 (M+H)+.

Aufarbeitung

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic phases were washed with water and brine
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (8 g silica gel; DCM/heptane 50:50 to 70:30)

Quellen und Nachweise

ORD-Eintrag
ord-1f53a45b2eda414ba82e446c03cc8d7e
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07259183B2

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