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Potassium Carbonate → 1-(4-{[(3,4-Dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-4-methoxyisoquinoline-3-carboxylic acid

HRID 2234023
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2234023
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH3:13])=[C:4]([C:14]([O:16]CC)=[O:15])[N:3]=1.FC(F)(F)C([O-])=O.[Cl:26][C:27]1[C:31]([Cl:32])=[C:30]([CH3:33])[NH:29][C:28]=1[C:34]([NH:36][CH:37]1[CH2:42][CH2:41][NH2+:40][CH2:39][CH2:38]1)=[O:35].C([O-])([O-])=O.[K+].[K+]>C(O)(C)(C)C>[Cl:26][C:27]1[C:31]([Cl:32])=[C:30]([CH3:33])[NH:29][C:28]=1[C:34]([NH:36][CH:37]1[CH2:42][CH2:41][N:40]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([O:12][CH3:13])=[C:4]([C:14]([OH:16])=[O:15])[N:3]=2)[CH2:39][CH2:38]1)=[O:35]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 685798674-{[(3,4-Dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidinium trifluoroacetate2×HCID 86038348Ethyl 1-chloro-4-methoxyisoquinoline-3-carboxylate

Produkt 1

HCID 685794921-(4-{[(3,4-Dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-4-methoxyisoquinoline-3-carboxylic acidAusbeute 1,8 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6386tert-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
170 °C

Versuchsvorschrift

In a sealed high pressure container with a Teflon lining was combined ethyl 1-chloro-4-methoxyisoquinoline-3-carboxylate (EP 650961 A1; 390 mg, 1.55 mmol), 4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidinium trifluoroacetate (Intermediate 86; 1.7 g, 4.4 mmol), and K2CO3 (2.2 g) in 20 ml tert-butanol. The container was heated at 170° C. with stirring for 8 hours. The solution was concentrated by rotary evaporation and reconstituted with EtOAc. The organic layer was washed 4× with H2O, and dried over MgSO4. Crude ethyl 1-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-4-methoxyisoquinoline-3-carboxylate was purified by reverse phase Si yielding 20 mg of the intermediate ester. The ethyl ester was then hydrolyzed as in Example 262 to yield 13.5 mg white solid final product.

Aufarbeitung

  1. concentrationThe solution was concentrated by rotary evaporation
  2. washThe organic layer was washed 4× with H2O
  3. dry with materialdried over MgSO4
  4. customCrude ethyl 1-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-4-methoxyisoquinoline-3-carboxylate was purified by reverse phase Si yielding 20 mg of the intermediate ester

Quellen und Nachweise

ORD-Eintrag
ord-4da3fb760a3945d2990f2f5807e3a7b5
Quelldatensatz
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07709503B2

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