Trifluoroacetic acid → 1-(5-Phenyl-1,3,4,5-tetrahydro-pyrido[4,3-b]indol-2-yl)-2-(4,7-dimethoxy-6-azaindol-3-yl)-ethane-1,2-dione

HRID 269962

Reaktionsgleichung

Reaktionsgleichung von HRID 269962
C(O[C:6]([N:8]1[CH2:26][CH2:25][C:11]2[N:12]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[C:10]=2[CH2:9]1)=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O.[CH3:34][O:35][C:36]1[CH:44]=[N:43][C:42]([O:45][CH3:46])=[C:41]2[C:37]=1[C:38]([C:47](=[O:51])C(O)=O)=[CH:39][NH:40]2.CCN(C(C)C)C(C)C.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1>C(Cl)Cl>[C:19]1([N:12]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[C:10]3[CH2:9][N:8]([C:6](=[O:7])[C:47]([C:38]4[C:37]5[C:41](=[C:42]([O:45][CH3:46])[N:43]=[CH:44][C:36]=5[O:35][CH3:34])[NH:40][CH:39]=4)=[O:51])[CH2:26][CH2:25][C:11]2=3)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

7

Edukt 5

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 224762342-(4,7-dimethoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetic acidHCID 693140455-Phenyl-1,3,4,5-tetrahydro-pyrido[4,3-b]indole-2-carboxylic acid tert-butyl ester

Produkt 1

HCID 117199471-(5-Phenyl-1,3,4,5-tetrahydro-pyrido[4,3-b]indol-2-yl)-2-(4,7-dimethoxy-6-azaindol-3-yl)-ethane-1,2-dioneAusbeute 33,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

General Method: A solution of 5-phenyl-1,3,4,5-tetrahydro-pyrido[4,3-b]indole-2-carboxylic acid tert-butyl ester (0.054 g, 0.155 mmol) in dry CH2Cl2 (2 mL) was treated with TFA (0.20 mL). After stirring the mixture for 1 h, the solvent was evaporated in vacuo and the residue was dissolved in CHCl3 (5 mL). To this mixture was added 4,7-dimethoxy-6-azaindol-3-yl-oxoacetic acid (0.042 g, 0.155 mmol), i-Pr2NEt (0.27 mL, 1.55 mmol) and then BOP-Cl (0.039 g, 0.153 mmol). The mixture was allowed to stir at room temperature for 2 h and then the solvent was removed in vacuo. The residue was partitioned with EtOAc-H2O, the organic phase was separated and the aqueous phase was re-extracted with EtOAc (2×). The combined organic layers were washed (H2O, brine), dried (Na2SO4) and evaporated. The residue was purified by preparative HPLC to give the title compound (0.025 g, 33%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 9.27 (s, 0.67H), 9.22 (s, 0.33H), 8.06 (d, J=3.0 Hz, 0.67H), 8.00 (d, J=3.0 Hz, 0.33H), 7.59-7.07 (m, 10H), 4.11 (m, 1H), 4.05 (s, 3H), 3.88 (s, 1H), 3.85 (m, 2H), 3.72 (s, 2H), 2.88 (m, 1H), 2.78 (m, 2H); LCMS: m/e 481 (M+H)+.

Aufarbeitung

  1. customthe solvent was evaporated in vacuo
  2. dissolutionthe residue was dissolved in CHCl3 (5 mL)
  3. stirringto stir at room temperature for 2 h
  4. customthe solvent was removed in vacuo
  5. customThe residue was partitioned with EtOAc-H2O
  6. customthe organic phase was separated
  7. extractionthe aqueous phase was re-extracted with EtOAc (2×)
  8. washThe combined organic layers were washed (H2O, brine)
  9. dry with materialdried (Na2SO4)
  10. customevaporated
  11. customThe residue was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-32c6e73a80334a2487126151c711854f
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07449476B2

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