Cesium carbonate → (4'-(6-chloro-2-(((3R,5 S,6R)-5-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)oxy)-1H-imidazo[4,5-b]pyridin-5-yl)-[1,1'-biphenyl]-4-yl)((R)-3-hydroxypyrrolidin-1-yl)methanone

HRID 1050262노트

반응식

HRID 1050262 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[N:38](COCC[Si](C)(C)C)[C:37](S(C)(=O)=O)=[N:36][C:5]2=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([N:22]3[CH2:26][CH2:25][C@@H:24]([O:27]COCC[Si](C)(C)C)[CH2:23]3)=[O:21])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1.C1(C2[O:62][C@H:61]3[CH2:63][C@@H:64]([OH:67])[CH2:65][O:66][C@@H:60]3[CH2:59][O:58]2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[NH:38][C:37]([O:67][C@@H:64]3[CH2:63][C@H:61]([OH:62])[C@@H:60]([CH2:59][OH:58])[O:66][CH2:65]3)=[N:36][C:5]2=[N:6][C:7]=1[C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([N:22]3[CH2:26][CH2:25][C@@H:24]([OH:27])[CH2:23]3)=[O:21])=[CH:16][CH:15]=2)=[CH:12][CH:13]=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 217656031,5-Anhydro-4,6-O-benzylidene-3-deoxy-D-glucitolHCID 90060767[4-[4-[6-chloro-2-methylsulfonyl-1-(2-trimethylsilylethoxymethyl)imidazo[4,5-b]pyridin-5-yl]phenyl]phenyl]-[(3R)-3-(2-trimethylsilylethoxymethoxy)pyrrolidin-1-yl]methanone

생성물 1

HCID 73332561(4'-(6-chloro-2-(((3R,5 S,6R)-5-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)oxy)-1H-imidazo[4,5-b]pyridin-5-yl)-[1,1'-biphenyl]-4-yl)((R)-3-hydroxypyrrolidin-1-yl)methanone

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of (R)-(4′-(6-chloro-2-(methylsulfonyl)-1-((2 (trimethylsilyl)ethoxy)-methyl)-1H-imidazo[4,5-b]pyridin-5-yl)-[1,1′-biphenyl]-4-yl)(3-((2-(trimethylsilyl)-ethoxy)methoxy)pyrrolidin-1-yl)methanone (150 mg, 0.198 mmol) and (4aR,7R,8aS)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-ol (100 mg, 0.423 mmol) in DMF (2 mL), was added cesium carbonate (150 mg, 0.460 mmol). The reaction mixture was stirred at room temperature for 2 h, then partitioned between water and EtOAc. The organic layer was separated and washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The chromatography of the resulting residue over silica (preparative TLC) eluting with 25% EtOAc in Hexanes afforded the title compound (Rf:0.7) LC-MS: calculated for C48H61ClN4O8Si2 912.37, observed m/e: 913.6 (M+H)+ (Rt: 3.30/4 min)

후처리

  1. custompartitioned between water and EtOAc
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. washThe chromatography of the resulting residue over silica (preparative TLC) eluting with 25% EtOAc in Hexanes

출처 및 근거

ORD 기록
ord-7a9cf4f6c94b48098202a4a15d32fdb6
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09382243B2

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