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 609871

反応式

HRID 609871 の反応式
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]

参加物

8

反応物 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

生成物 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-one収率 95%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-801b13aa76c44f8db276258d42b7e442
出典データセット
uspto-grants-1999_12
特許番号
US05998432

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