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 926630노트

반응식

HRID 926630 반응식
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

참가 물질

5

반응물 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

생성물 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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-8586eeaa791d43c48301d1fb9973dd91
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09284308B2

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