Formic Acid → azetidin-3-yl(4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methanol

HRID 926630Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 926630
C(OC([N:8]1[CH2:11][CH:10]([C:12]([C:20]2[CH:21]=[C:22]3[C:27](=[CH:28][CH:29]=2)[N:26]=[C:25]([O:30][CH3:31])[C:24]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][CH:34]=2)=[C:23]3[Cl:43])([OH:19])[C:13]2[N:17]([CH3:18])[N:16]=[N:15][CH:14]=2)[CH2:9]1)=O)(C)(C)C.C(O)=O.Cl>CO>[NH:8]1[CH2:11][CH:10]([C:12]([C:20]2[CH:21]=[C:22]3[C:27](=[CH:28][CH:29]=2)[N:26]=[C:25]([O:30][CH3:31])[C:24]([CH2:32][C:33]2[CH:34]=[CH:35][C:36]([C:39]([F:41])([F:40])[F:42])=[CH:37][CH:38]=2)=[C:23]3[Cl:43])([C:13]2[N:17]([CH3:18])[N:16]=[N:15][CH:14]=2)[OH:19])[CH2:9]1

Komponenten

5

Edukt 3

HCID 284Formic AcidHCID 313Hydrochloric AcidHCID 86715661tert-Butyl-3-((4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(hydroxy)(1-methyl-1H-1,2,3-triazol-5-yl)methyl)azetidine-1-carboxylate

Produkt 1

HCID 86715675azetidin-3-yl(4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a flask containing tert-butyl 3-((4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(hydroxy)(1-methyl-1H-1,2,3-triazol-5-yl)methyl)azetidine-1-carboxylate (165 mg, 0.27 mmol, Example 123) was added formic acid (5 mL) at room temperature followed by 6 N aqueous HCl (0.21 mL). The mixture was stirred at room temperature for 40 minutes and then MeOH (5 mL) was added and the mixture was stirred for 20 minutes before concentrating. The resulting oil was chromatographed directly on silica gel (10% 2 M NH3-MeOH-DCM increasing to 12% 2 M NH3-MeOH) to provide the title compound as an off white powder. 1H NMR (500 MHz, CDCl3) δ 8.30 (d, J=2.1 Hz, 1H), 8.20 (s, 1H), 7.92 (s, 1H), 7.76 (d, J=8.8 Hz, 1H), 7.47 (d, J=8.1 Hz, 2H), 7.42-7.32 (m, 3H), 4.52-4.34 (m, 2H), 4.33-4.16 (m, 3H), 4.05 (s, 3H), 3.96-3.80 (m, 1H), 3.71 (s, 4H); MS (ESI): mass calcd. Chemical Formula: C25H23ClF3N5O2; Exact Mass: 517.2. m/z found 517.9 [M+H]+.

Aufarbeitung

  1. stirringthe mixture was stirred for 20 minutes
  2. concentrationbefore concentrating
  3. customThe resulting oil was chromatographed directly on silica gel (10% 2 M NH3-MeOH-DCM increasing to 12% 2 M NH3-MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-8586eeaa791d43c48301d1fb9973dd91
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09284308B2

Notizen zur Reaktion

Wird geladen…