Cesium carbonate → tert-butyl 4-[(6'-amino-5'-{(1R)-1-[5-fluoro-2-(2H-1,2,3-triazol-2-yl)phenyl]ethoxy}-3,3'-bipyridin-6-yl)oxy]piperidine-1-carboxylate

HRID 1406319노트

반응식

HRID 1406319 반응식
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][C:11]([OH:14])=[CH:12][CH:13]=2)=[CH:4][C:3]=1[O:15][C@@H:16]([C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1[N:25]1[N:29]=[CH:28][CH:27]=[N:26]1)[CH3:17].CS(O[CH:35]1[CH2:40][CH2:39][N:38]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:37][CH2:36]1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>[Cl-].[Na+].O>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][C:11]([O:14][CH:35]3[CH2:40][CH2:39][N:38]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:37][CH2:36]3)=[CH:12][CH:13]=2)=[CH:4][C:3]=1[O:15][C@@H:16]([C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1[N:25]1[N:29]=[CH:28][CH:27]=[N:26]1)[CH3:17]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidineHCID 178462223HCID 178462223, 화합물

생성물 1

HCID 67468730tert-butyl 4-[(6'-amino-5'-{(1R)-1-[5-fluoro-2-(2H-1,2,3-triazol-2-yl)phenyl]ethoxy}-3,3'-bipyridin-6-yl)oxy]piperidine-1-carboxylate수율 66%

시약·촉매·용매 1

HCID 57417360Sodium chloride; water용매

실험 절차

A mixture of example 121 (125 mg, 0.308 mmol), tert-butyl 4-(methylsulfonyloxy)piperidine-1-carboxylate (129 mg, 0.462 mmol) and cesium carbonate (301 mg, 0.924 mmol) was heated at 90° C. for 24 hr. LCMS indicated ˜90% completion of the reaction. Two products were observed. The mixture was dropped into brine and the resulting precipitate was collected by filtration and rinsed with water. The partially dried solids were taken up in EtOAc, dried over magnesium sulfate and concentrated. The residue was purified with a Biotage silica gel cartridge eluting with 50-100% EtOAc/Heptane to give tert-butyl 4-[(6′-amino-5′-{(1R)-1-[5-fluoro-2-(2H-1,2,3-triazol-2-yl)phenyl]ethoxy}-3,3′-bipyridin-6-yl)oxy]piperidine-1-carboxylate (117 mg).

후처리

  1. custom˜90% completion of the reaction
  2. filtrationthe resulting precipitate was collected by filtration
  3. washrinsed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified with a Biotage silica gel cartridge
  7. washeluting with 50-100% EtOAc/Heptane

출처 및 근거

ORD 기록
ord-1e630e622f3c4edb901cb87c63b794ee
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08916593B2

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