1,2-Dichloroethane → N-(3-cyanobenzyl)-2N-(4-chlorophenylaminocarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide

HRID 1432541Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1432541
ClC1C=CC(NC([CH:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14][CH:13]([C:21]([OH:23])=O)[NH:12]2)=O)=CC=1.[C:24]([C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH2:29][NH2:30])#[N:25].[CH2:34]([Cl:37])[CH2:35]Cl.[OH2:38]>CN(C=O)C.CCOC(C)=O.CO.C(Cl)Cl.CCOC(C)=O>[C:24]([C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH2:29][NH:30][C:21]([CH:13]1[CH2:14][C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:11][N:12]1[C:11]([NH:12][C:13]1[CH:21]=[CH:35][C:34]([Cl:37])=[CH:15][CH:14]=1)=[O:38])=[O:23])#[N:25]

Komponenten

8

Edukt 4

HCID 111,2-DichloroethaneHCID 962WaterHCID 457594Benzonitrile, 3-(aminomethyl)-HCID 131727716(4-Chlorophenylaminocarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

Produkt 1

HCID 86606516N-(3-cyanobenzyl)-2N-(4-chlorophenylaminocarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 21901258Dichloromethane ethyl acetate methanolLösungsmittel

Versuchsvorschrift

To a solution of 2N-(4-chlorophenylaminocarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (291 mg, 0.880 mmol) and 3-cyanobenzylamine (140 mg, 1.06 mmol) in DMF (7 mL), EDC (254 mg, 1.32 mmol) was added. The mixture was then stirred at room temperature overnight. H2O and EtOAc were added. The organic layer was separated, washed with 1N HCl, dried over Na2SO4, concentrated in vacuo to give a solid. After being trituated with EtOAc/MeOH/CH2Cl2, the white solid was collected, dried on vacuum (148 mg), which was pure enough for the next reaction.

Aufarbeitung

  1. customThe organic layer was separated
  2. washwashed with 1N HCl
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto give a solid
  6. customthe white solid was collected
  7. customdried on vacuum (148 mg), which
  8. customwas pure enough for the next reaction

Quellen und Nachweise

ORD-Eintrag
ord-83afb3a3ec9a4e74a4f0d8c940da6a62
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612089B2

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