4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride → 5-(1h-Indol-3-yl)pentanoic acid [(4-dimethylamino-4-phenylcyclohexylcarbamoyl)-methyl]amide

HRID 1394240Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1394240
[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]([CH2:52][CH2:53][CH3:54])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])[CH2:54][CH2:53][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 230230012-(1H-indol-3-yl)pentanoic acidHCID 692169152-Amino-n-(4-dimethylamino-4-phenylcyclohexyl)acetamide

Produkt 1

HCID 129862575-(1h-Indol-3-yl)pentanoic acid [(4-dimethylamino-4-phenylcyclohexylcarbamoyl)-methyl]amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

The more nonpolar diastereomer of 2-amino-N-(4-dimethylamino-4-phenylcyclohexyl)-acetamide (276 mg, 1.0 mmole) and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (415 mg, 1.5 mmole) were added to a solution of indol-3-yl-pentanoic acid (217 mg, 1.0 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 nonpolar amide was obtained as a colorless oil in a yield of 474 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-56a364806e8e40f489299e512731fbea
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07348354B2

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