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 929213ノート

反応式

HRID 929213 の反応式
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

参加物

6

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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)

後処理

  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)

出典と根拠

ORDレコード
ord-4a365d753d3842d4a554313552fba4c0
出典データセット
uspto-grants-2016_03
特許番号
US09290517B2

反応ノート

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