2-Mercaptobenzoic Acid → N-(2-{2-Methyl-4-[((S)-phenyl-(S)-piperidin-2-yl-methyl)-amino]-quinolin-8-yloxy}-ethyl)methanesulfonamide dihydrochloride

HRID 1966526Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1966526
C1(P(C2C=CC=CC=2)CCCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([N:34]1[CH2:39][CH2:38][CH2:37][CH2:36][C@H:35]1[C@@H:40]([NH:47][C:48]1[C:57]2[C:52](=[C:53]([O:58][CH2:59][CH2:60][NH:61][S:62]([CH3:65])(=[O:64])=[O:63])[CH:54]=[CH:55][CH:56]=2)[N:51]=[C:50]([CH3:66])[CH:49]=1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)C=C.SC1C=CC=CC=1C(O)=O.[OH-].[Na+].C(O)(C)C.O.[ClH:84]>C1COCC1>[ClH:84].[ClH:84].[CH3:66][C:50]1[CH:49]=[C:48]([NH:47][C@@H:40]([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[C@@H:35]2[CH2:36][CH2:37][CH2:38][CH2:39][NH:34]2)[C:57]2[C:52](=[C:53]([O:58][CH2:59][CH2:60][NH:61][S:62]([CH3:65])(=[O:63])=[O:64])[CH:54]=[CH:55][CH:56]=2)[N:51]=1

Komponenten

7

Edukt 5

HCID 54432-Mercaptobenzoic AcidHCID 14798Sodium HydroxideHCID 821241,4-Bis(diphenylphosphino)butaneHCID 21409480Isopropanol-hcl-waterHCID 59474734N-[2-(4-{[(S)-((S)-1-Allylpiperidin-2-yl)-phenylmethyl]-amino}-2-methylquinolin-8-yloxy)ethyl]methanesulfonamide

Produkt 1

HCID 68498582N-(2-{2-Methyl-4-[((S)-phenyl-(S)-piperidin-2-yl-methyl)-amino]-quinolin-8-yloxy}-ethyl)methanesulfonamide dihydrochlorideAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

Tris-(dibenzylidenaceton)-dipalladium(0) (19.0 mg, 0.021 mmole) and 1,4-bis(diphenylphosphino)butane (9 mg, 0.021 mmole) were mixed with THF (10 mL). N-[2-(4-{[(S)—((S)-1-Allylpiperidin-2-yl)-phenylmethyl]-amino}-2-methylquinolin-8-yloxy)-ethyl]-methanesulfonamide (example 35, 130 mg, 0.256 mmole) in THF (5 mL) and 2-mercaptobenzoic acid (86.7 mg, 0.562 mmole) in THF (5 mL) were added and the mixture was stirred at RT for 2 hrs. The content of the flask was mixed with 1N NaOH and extracted with dichloromethane. The organic layer was washed with water and saturated NaCl solution and concentrated. The residue thus obtained was cystallized from isopropanol/water/HCl to obtain a white solid (42 mg, 30%).

Aufarbeitung

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed with water and saturated NaCl solution
  3. concentrationconcentrated
  4. customThe residue thus obtained

Quellen und Nachweise

ORD-Eintrag
ord-69cc82f3695b4a3b8d63c256525f999d
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08420670B2

Notizen zur Reaktion

Wird geladen…