Water → (3R,3aR,6aR)-6-(2-((5-([1,1'-biphenyl]-4-yl)-6-chloro-1H-imidazo[4,5-b]pyridin-2-yl)oxy)ethyl)hexahydrofuro[3,2-b]furan-3-ol

HRID 929213노트

반응식

HRID 929213 반응식
N1CCCN2CCCCCC=12.[C:12]1([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:17]=[CH:16][C:15]([C:18]2[N:23]=[C:22]3[N:24]=[C:25](S(C)(=O)=O)[N:26](COCC[Si](C)(C)C)[C:21]3=[CH:20][C:19]=2[Cl:39])=[CH:14][CH:13]=1.[Si]([O:53][C@H:54]1[C@H:58]2[O:59][CH2:60][CH:61]([CH2:62][CH2:63][OH:64])[C@H:57]2[O:56][CH2:55]1)(C(C)(C)C)(C)C.O>CN(C=O)C>[C:12]1([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:17]=[CH:16][C:15]([C:18]2[N:23]=[C:22]3[N:24]=[C:25]([O:64][CH2:63][CH2:62][CH:61]4[C@H:57]5[O:56][CH2:55][C@@H:54]([OH:53])[C@H:58]5[O:59][CH2:60]4)[NH:26][C:21]3=[CH:20][C:19]=2[Cl:39])=[CH:14][CH:13]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 682826082-[[6-Chloro-2-methylsulfonyl-5-(4-phenylphenyl)imidazo[4,5-b]pyridin-1-yl]methoxy]ethyl-trimethyl-silaneHCID 900420242-((3aR,6R,6aS)-6-((tert-butyldimethylsilyl)oxy)hexahydrofuro[3,2-b]furan-3-yl)ethanol

생성물 1

HCID 90067536(3R,3aR,6aR)-6-(2-((5-([1,1'-biphenyl]-4-yl)-6-chloro-1H-imidazo[4,5-b]pyridin-2-yl)oxy)ethyl)hexahydrofuro[3,2-b]furan-3-ol

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine (0.019 ml, 0.128 mmol) was added to a stirred mixture of 5-([1,1′-biphenyl]-4-yl)-6-chloro-2-(methylsulfonyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazo[4,5-b]pyridine (52.6 mg, 0.102 mmol) and 2-((3aR,6R,6aS)-6-((tert-butyldimethylsilyl)-oxy)hexahydro-furo[3,2-b]furan-3-yl)ethanol (38.4 mg, 0.133 mmol) in DMF (1 ml) and the mixture was stirred at room temperature overnight. Water (20 mL) was added and the mixture was extracted with ethyl acetate (2×30 mL). The combined organic fractions were washed with brine (saturated, 20 mL), dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative TLC, eluting with EtOAc/isohexane (1:1) to give the title compound. LC-MS: calculated for C38H52ClN3O5Si2 721.31 observed m/e: 722.39 (M+H)+ (Rt 1.58/2 min)

후처리

  1. extractionthe mixture was extracted with ethyl acetate (2×30 mL)
  2. washThe combined organic fractions were washed with brine (saturated, 20 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated under reduced pressure
  6. customThe resulting residue was purified by preparative TLC
  7. washeluting with EtOAc/isohexane (1:1)

출처 및 근거

ORD 기록
ord-4a365d753d3842d4a554313552fba4c0
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290517B2

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