Reaktion #1453923

ord-9d1c99598d674130a6e7095968db9a33

Reaktionsgleichung

Nc1nccc2cc(O)ccc12
1-amino-6-hydroxyisoquinoline
CC(C)(C)OC(=O)N[C@H]1CC[C@H](OS(C)(=O)=O)CC1
methane-sulfonic acid trans-4-tert-butoxycarbonylaminocyclohexyl ester
CCN(CC)P1(=NC(C)(C)C)NCCCN1C
2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine on polystyrene
→
CC(C)(C)OC(=O)N[C@H]1CC[C@@H](Oc2ccc3c(N)nccc3c2)CC1
cis-[4-(1-aminoisoquinolin-6-yloxy)cyclohexyl]carbamic acid tert-butyl ester
Ausbeute 7.8%

Edukte

Nc1nccc2cc(O)ccc12
1-amino-6-hydroxyisoquinoline
CC(C)(C)OC(=O)N[C@H]1CC[C@H](OS(C)(=O)=O)CC1
methane-sulfonic acid trans-4-tert-butoxycarbonylaminocyclohexyl ester
CCN(CC)P1(=NC(C)(C)C)NCCCN1C
2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine on polystyrene

Reagenzien

Keine

Lösungsmittel

CC#N
acetonitrile

Reaktionsbedingungen

Temperatur
120°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigewas removed by filtration
  2. 2
    Waschenwashing with acetonitrile
  3. 3
    Sonstigethe filtrate evaporated to dryness under reduced pressure
  4. 4
    SonstigePurification

Vorschrift

A suspension of 1-amino-6-hydroxyisoquinoline (0.08 g, 0.5mmol), methane-sulfonic acid trans-4-tert-butoxycarbonylaminocyclohexyl ester (176 mg) and 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine on polystyrene (270mg, ˜2.2 mmol/g loading) in acetonitrile (2ml) were heated at 120° C. over a period of 15 minutes using the microwave. The excess supported reagent was removed by filtration, washing with acetonitrile followed by methanol, and the filtrate evaporated to dryness under reduced pressure. Purification was achieved by prep-HPLC to give cis-[4-(1-aminoisoquinolin-6-yloxy)cyclohexyl]carbamic acid tert-butyl ester (14 mg).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07893088B2uspto-grants-2011_02