4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride → N-[(4-dimethylamino-4-phenylcyclohexylcarbamoyl)methyl]-3-(1H-indol-3-yl)propionamide

HRID 1394245Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1394245
[NH2:1][CH2:2][C:3]([NH:5][CH:6]1[CH2:11][CH2:10][C:9]([N:18]([CH3:20])[CH3:19])([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)=[O:4].[Cl-].[CH3:22][O:23]C1N=C(OC)N=C([N+]2(C)CCOCC2)N=1.[NH:39]1[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[C:41]([CH:48]([CH3:52])C(O)=O)=[CH:40]1>CO>[CH3:19][N:18]([CH3:20])[C:9]1([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:10][CH2:11][CH:6]([NH:5][C:3]([CH2:2][NH:1][C:22](=[O:23])[CH2:52][CH2:48][C:41]2[C:42]3[C:47](=[CH:46][CH:45]=[CH:44][CH:43]=3)[NH:39][CH:40]=2)=[O:4])[CH2:7][CH2:8]1

Komponenten

5

Edukt 3

HCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 108994232-(1H-indol-3-yl)propanoic acidHCID 692169152-Amino-n-(4-dimethylamino-4-phenylcyclohexyl)acetamide

Produkt 1

HCID 69216416N-[(4-dimethylamino-4-phenylcyclohexylcarbamoyl)methyl]-3-(1H-indol-3-yl)propionamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

The more polar diastereomer of 2-amino-N-(4-dimethylamino-4-phenylcyclohexyl)-acetamide (159 mg, 0.57 mmole) and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (239 mg, 0.86 mmole) were added to a solution of indol-3-yl-propionic acid (109 mg, 0.57 mmole) in MeOH and stirred for 24 h at room temperature. Working up was performed by removing MeOH by distillation. The batch was re-dissolved with water, adjusted to pH 11 with 5M NaOH and extracted with ethyl acetate. The organic phase was dried with Na2SO4 and evaporated. The more polar amide was obtained as a colorless oil in a yield of 257 mg (100%).

Aufarbeitung

  1. customby removing MeOH
  2. distillationby distillation
  3. dissolutionThe batch was re-dissolved with water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic phase was dried with Na2SO4
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-95bdee8149a4439091629fd959cf8ffb
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07348354B2

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