Trifluoroacetic acid → Piperidine, 1-[2-[4-methoxy-7-(3-methyl-1H-pyrazol-5-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-1,2-dioxoethyl]-4-[(5-methyl-1,3,4-oxadiazol-2-yl)phenylmethylene]-

HRID 1394458노트

반응식

HRID 1394458 반응식
C([O:5][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)(C)(C)C.[C:27](O)(C(F)(F)F)=O.Cl.[CH3:35][O:36][C:37]1[CH:45]=[N:44][C:43]([C:46]2[CH:47]=[CH:48][N:49](C)[N:50]=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[CH2:10][CH2:9][N:8]([C:6](=[O:5])[C:52]([C:39]3[C:38]4[C:42](=[C:43]([C:46]5[CH:47]=[C:48]([CH3:27])[NH:49][N:50]=5)[N:44]=[CH:45][C:37]=4[O:36][CH3:35])[NH:41][CH:40]=3)=[O:56])[CH2:13][CH2:12]2)[C:15]2[O:16][C:17]([CH3:20])=[N:18][N:19]=2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=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 670465744-Methoxy-7-(2-methylpyrazol-5-yl)-6-azaindol-3-yl-oxoacetic acid hydrochloride salt

생성물 1

HCID 5279947Piperidine, 1-[2-[4-methoxy-7-(3-methyl-1H-pyrazol-5-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-1,2-dioxoethyl]-4-[(5-methyl-1,3,4-oxadiazol-2-yl)phenylmethylene]-수율 6%

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 (0.0430 g, 0.167 mmol) in CH2Cl2 (2 mL) was added TFA (0.3 mL) and the reaction mixture was stirred for 30 min. The solvent was then removed in vacuo and the residual material was dissolved in CHCl3 (2 mL). To this solution was added 4-methoxy-7-(2-methylpyrazol-5-yl)-6-azaindol-3-yl-oxoacetic acid hydrochloride salt (0.050 g, 0.167 mmol) and iPrNEt2 (0.145 mL, 0.833 mmol), followed by BOP—Cl (0.0590 g, 0.233 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 (TFA) to give the title compound (0.0053 g, 6%) as a colorless solid:

후처리

  1. customThe solvent was then removed in vacuo
  2. dissolutionthe residual material was dissolved in CHCl3 (2 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 (TFA)

출처 및 근거

ORD 기록
ord-fa8a2901711a4ba78d92c677bd0053c0
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07348337B2

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