Trifluoroacetic acid → 1-[4-methoxy-7-(4-methyltriazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-2-[4-[(5-methyl-1,3,4-oxadiazol-2-yl)-phenyl-methylene]-1-piperidyl]ethane-1,2-dione

HRID 606773노트

반응식

HRID 606773 반응식
C(O[C:6]([N:8]1[CH2:13][CH2:12][C:11](=[C:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[O:16][C:17]([CH3:20])=[N:18][N:19]=2)[CH2:10][CH2:9]1)=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O.Cl.[CH3:35][O:36][C:37]1[CH:45]=[N:44][C:43]([N:46]2[CH:50]=[C:49]([CH3:51])[N:48]=[N:47]2)=[C:42]2[C:38]=1[C:39]([C:52](=[O:56])C(O)=O)=[CH:40][NH:41]2.C(N(CC)CC)(C)C.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1>C(Cl)Cl>[C:21]1([C:14](=[C:11]2[CH2:12][CH2:13][N:8]([C:6](=[O:7])[C:52]([C:39]3[C:38]4[C:42](=[C:43]([N:46]5[CH:50]=[C:49]([CH3:51])[N:48]=[N:47]5)[N:44]=[CH:45][C:37]=4[O:36][CH3:35])[NH:41][CH:40]=3)=[O:56])[CH2:9][CH2:10]2)[C:15]2[O:16][C:17]([CH3:20])=[N:18][N:19]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

참가 물질

7

반응물 5

HCID 6422Trifluoroacetic acidHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 521913N,N-Diethyl-2-propanamineHCID 670464714-[1-Phenyl-1-(5-methyl-1,3,4-oxadiazol-2-yl)methylene]-piperidine-1-carboxylic acid tert-butyl esterHCID 670465684-Methoxy-7-(4-methyl-1,2,3-triazol-1-yl)-6-azaindol-3-yl-oxoacetic acid hydrochloride salt

생성물 1

HCID 52799451-[4-methoxy-7-(4-methyltriazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-2-[4-[(5-methyl-1,3,4-oxadiazol-2-yl)-phenyl-methylene]-1-piperidyl]ethane-1,2-dione수율 39%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 4-[1-phenyl-1-(5-methyl-1,3,4-oxadiazol-2-yl)methylene]piperidine-1-carboxylic acid tert-butyl ester (0.0300 g, 0.084 mmol) in CH2Cl2 (1 mL) was added TFA (0.4 mL) and the reaction mixture was stirred at rt for 30 min. The solvent was subsequently removed in vacuo and the material was dissolved in CHCl3 (3 mL). To this solution was then added 4-methoxy-7-(4-methyl-1,2,3-triazol-1-yl)-6-azaindol-3-yl-oxoacetic acid hydrochloride salt (0.0250 g, 0.084 mmol) and iPrNEt2 (0.059 mL, 0.338 mmol), followed by BOP-Cl (0.0210 g, 0.084 mmol). The mixture was allowed to stir at rt for 2 h and then the solvent was removed in vacuo. The residue was diluted with H2O and extracted with EtOAc (×3). The combined organic layers were washed (H2O, brine), dried (Na2SO4) and concentrated, and the residue was purified by preparative HPLC (NH4OAc) affording the title compound (0.0174 g, 39%) as a colorless solid:

후처리

  1. customThe solvent was subsequently removed in vacuo
  2. dissolutionthe material was dissolved in CHCl3 (3 mL)
  3. stirringto stir at rt for 2 h
  4. customthe solvent was removed in vacuo
  5. additionThe residue was diluted with H2O
  6. extractionextracted with EtOAc (×3)
  7. washThe combined organic layers were washed (H2O, brine)
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated
  10. customthe residue was purified by preparative HPLC (NH4OAc)

출처 및 근거

ORD 기록
ord-a6b633f4cf0544719739ff16aa53cf35
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915283B2

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