Hydrochloric Acid → 3'-Hydroxy-biphenyl-4-carboxylic acid 3-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-7-ylcarbamoyl)-benzylamide

HRID 2367737Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2367737
C(O[C:6](=[O:29])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15](=[O:28])[NH:16][C:17]2[CH:26]=[C:25]3[C:20]([CH2:21][CH2:22][N:23]([CH3:27])[CH2:24]3)=[CH:19][CH:18]=2)[CH:10]=1)(C)(C)C.[ClH:30].[O:31]1[CH2:36][CH2:35]OCC1.[CH3:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42]>C(Cl)Cl.CCOCC>[CH3:27][N:23]1[CH2:22][CH2:21][C:20]2[C:25](=[CH:26][C:17]([NH:16][C:15]([C:11]3[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=3)[CH2:8][NH:7][C:6]([C:39]3[CH:38]=[CH:37][C:42]([C:9]4[CH:10]=[CH:11][CH:35]=[C:36]([OH:31])[CH:8]=4)=[CH:41][CH:40]=3)=[O:29])=[O:28])=[CH:18][CH:19]=2)[CH2:24]1.[ClH:30].[ClH:30].[NH2:7][CH2:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=1)[C:15]([NH:16][C:17]1[CH:26]=[C:25]2[C:20]([CH2:21][CH2:22][N:23]([CH3:27])[CH2:24]2)=[CH:19][CH:18]=1)=[O:28]

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 8058Hexane2×HCID 312751,4-DioxaneHCID 66656233[3-(2-Methyl-1,2,3,4-tetrahydro-isoquinolin-7-ylcarbamoyl)-benzyl]-carbamic acid tert-butyl ester

Produkt 2

HCID 566003433'-Hydroxy-biphenyl-4-carboxylic acid 3-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-7-ylcarbamoyl)-benzylamideHCID 666490723-(2-Methyl-1,2,3,4-tetrahydro-isoquinolin-7-ylcarbamoyl)benzylamine dihydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of [3-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-7-ylcarbamoyl)-benzyl]-carbamic acid tert-butyl ester (6.35 g, 15.6 mmol) in anhydrous DCM (250 mL) at rt add 4M HCl in 1,4-dioxane (58.4 mL, 233.6 mmol) and stir the reaction at rt for 24 h. Dilute the solid suspension with Et2O (500 mL) and hexane (800 mL), stir vigorously for 20 min then filter and wash with Et2O then hexane to afford the desired product 3-aminomethyl-N-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-7-yl)-benzamide dihydrochloride as a hydroscopic solid (5.68 g, 14.7 mmol).

Aufarbeitung

  1. customthe reaction at rt for 24 h
  2. stirringstir vigorously for 20 min
  3. filtrationthen filter
  4. washwash with Et2O

Quellen und Nachweise

ORD-Eintrag
ord-493bf1b0db74460397d6b3dde3fa9b6f
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697911B2

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