Water → 1-{2-[4-(9H-imidazo[1',2':1,2]imidazo[4,5-b]pyridin-9-yl)phenoxy]-1H-benzimidazol-1-yl}-2-methylpropan-2-ol

HRID 572182노트

반응식

HRID 572182 반응식
C[Mg]Br.[CH2:4]1COCC1.[N:9]1[CH:10]=[CH:11][N:12]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[N:14]([C:21]3[CH:40]=[CH:39][C:24]([O:25][C:26]4[N:30]([CH2:31][C:32](=[O:34])[CH3:33])[C:29]5[CH:35]=[CH:36][CH:37]=[CH:38][C:28]=5[N:27]=4)=[CH:23][CH:22]=3)[C:13]=12.O>C1COCC1>[N:9]1[CH:10]=[CH:11][N:12]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[N:14]([C:21]3[CH:22]=[CH:23][C:24]([O:25][C:26]4[N:30]([CH2:31][C:32]([CH3:4])([OH:34])[CH3:33])[C:29]5[CH:35]=[CH:36][CH:37]=[CH:38][C:28]=5[N:27]=4)=[CH:39][CH:40]=3)[C:13]=12

참가 물질

5

반응물 3

HCID 962WaterHCID 867049891-{2-[4-(9H-imidazo[1',2':1,2]imidazo[4,5-b]pyridin-9-yl)phenoxy]-1H-benzimidazol-1-yl}propan-2-oneHCID 178420675HCID 178420675, 화합물

생성물 1

HCID 683505881-{2-[4-(9H-imidazo[1',2':1,2]imidazo[4,5-b]pyridin-9-yl)phenoxy]-1H-benzimidazol-1-yl}-2-methylpropan-2-ol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a suspension of cerium chloride(III) (296 mg) in THF (4 ml) was added dropwise 1 M methylmagnesium bromide-THF solution (1.2 ml) at −78° C. After stirring for 10 min, a solution of 1-{2-[4-(9H-imidazo[1′,2′:1,2]imidazo[4,5-b]pyridin-9-yl)phenoxy]-1H-benzimidazol-1-yl}propan-2-one (338 mg) obtained in Example 10 in THF (20 ml) was added dropwise at −78° C., and the obtained mixture was warmed to room temperature. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was subjected to basic silica gel column chromatography (hexane/ethyl acetate), purified by HPLC (L-Column 2 ODS, 10 mM aqueous hydrogen carbonate ammonium-containing acetonitrile solution) and recrystallized from methanol/water to give the title compound (44.0 mg).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. custompurified by HPLC (L-Column 2 ODS, 10 mM aqueous hydrogen carbonate ammonium-containing acetonitrile solution)
  6. customrecrystallized from methanol/water

출처 및 근거

ORD 기록
ord-989d4094304248b5a670ebde80fa6552
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029388B2

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