Trifluoroacetic acid → HCID 178493776, Verbindung

HRID 1394450Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1394450
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[NH:19][N:18]=[C:17]([CH3:20])[CH:16]=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[NH:19][N:18]=[C:17]([CH3:20])[CH:16]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Komponenten

7

Edukt 5

HCID 6422Trifluoroacetic acidHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 521913N,N-Diethyl-2-propanamineHCID 670465684-Methoxy-7-(4-methyl-1,2,3-triazol-1-yl)-6-azaindol-3-yl-oxoacetic acid hydrochloride saltHCID 178423825HCID 178423825, Verbindung

Produkt 1

HCID 178493776HCID 178493776, VerbindungAusbeute 44,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-[1-phenyl-1-(3-methylpyrazol-5-yl)methylene]piperidine-1-carboxylic acid tert-butyl ester(0.0190 g, 0.0538 mmol) in CH2Cl2 (1 mL) was added TFA (0.4 mL) and the mixture was stirred at rt for 30 min. The solvent was then removed in vacuo and the material was dissolved in CHCl3 (2 mL). To this solution was added 4-methoxy-7-(4-methyl-1,2,3-triazol-1-yl)-6-azaindol-3-yl-oxoacetic acid hydrochloride salt (0.0187 g, 0.0621 mmol) and iPrNEt2 (0.050 mL, 0.287 mmol), followed by BOP—Cl (0.0221 g, 0.868 mmol). The mixture was allowed to stir at rt for 2 h and then the solvent was removed in vacuo. The resulting 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) to give the title compound (0.0128 g, 44%) as a colorless solid:

Aufarbeitung

  1. customThe solvent was then removed in vacuo
  2. dissolutionthe material was dissolved in CHCl3 (2 mL)
  3. stirringto stir at rt for 2 h
  4. customthe solvent was removed in vacuo
  5. additionThe resulting 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)

Quellen und Nachweise

ORD-Eintrag
ord-c2555b750e9e48039a6eece566b56725
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07348337B2

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