Hydrochloric Acid → (S)-1-(2-Azabicyclo[2.2.2]oct-2-yl)-2-[3-(2-benzyloxy-1-methylethyl)-2-(3,5-dimethylphenyl)-1H-pyrrolo[2,3-b]-pyridin-5-yl]-2-methylpropan-1-one

HRID 609871노트

반응식

HRID 609871 반응식
C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[CH2:34]([O:41][CH2:42][C@H:43]([C:45]1[C:53]2[C:48](=[N:49][CH:50]=[C:51]([C:54]([CH3:59])([CH3:58])[C:55]([OH:57])=O)[CH:52]=2)[NH:47][C:46]=1[C:60]1[CH:65]=[C:64]([CH3:66])[CH:63]=[C:62]([CH3:67])[CH:61]=1)[CH3:44])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[CH2:68]1[CH:73]2[CH2:74][NH:75][CH:70]([CH2:71][CH2:72]2)[CH2:69]1.Cl.C(N(CC)CC)C.O.[Cl-].[Na+].O>C(Cl)Cl>[CH:70]12[CH2:69][CH2:68][CH:73]([CH2:72][CH2:71]1)[CH2:74][N:75]2[C:55](=[O:57])[C:54]([C:51]1[CH:52]=[C:53]2[C:45]([C@H:43]([CH3:44])[CH2:42][O:41][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[C:46]([C:60]3[CH:61]=[C:62]([CH3:67])[CH:63]=[C:64]([CH3:66])[CH:65]=3)[NH:47][C:48]2=[N:49][CH:50]=1)([CH3:58])[CH3:59]

참가 물질

8

반응물 6

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 92362-Azabicyclo(2.2.2)octaneHCID 2724699PyBOPHCID 15887219(S)-2-[3-(2-Benzyloxy-1-methylethyl)-2-(3,5-dimethyl-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-methylpropanoic acidHCID 23713072Sodium chloride dihydrate

생성물 1

HCID 53953435(S)-1-(2-Azabicyclo[2.2.2]oct-2-yl)-2-[3-(2-benzyloxy-1-methylethyl)-2-(3,5-dimethylphenyl)-1H-pyrrolo[2,3-b]-pyridin-5-yl]-2-methylpropan-1-one수율 95%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

PyBOP (1.51 g, 2.89 mmol) was added to a stirred mixture of (S)-2-[3-(2-benzyloxy-1-methylethyl)-2-(3,5-dimethylphenyl)-1H-pyrrolo-[2,3-b]pyridin-5-yl]-2-methylpropanoic acid (1.20 g, 2.63 mmol), isoquinuclidine.HCl (0.78 g, 5.26 mmol) and triethylamine (1.47 mL, 10.5 mmol) in CH2Cl2 (26 mL) at ambient temperature. After approximately 12 h, the reaction mixture was poured into water/brine (1:1) and extracted with ethyl acetate (×3). The combined organic extract was washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (gradient eluton; 60-75% ethyl acetate/hexanes as eluent) to give the title compound as a colourless foam (1.37 g, 95% overall).

후처리

  1. customat ambient temperature
  2. extractionextracted with ethyl acetate (×3)
  3. extractionThe combined organic extract
  4. washwas washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography on silica gel (gradient eluton; 60-75% ethyl acetate/hexanes as eluent)

출처 및 근거

ORD 기록
ord-801b13aa76c44f8db276258d42b7e442
출처 데이터셋
uspto-grants-1999_12
특허 번호
US05998432

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