Imidazole → Methyl (S)-2-(3-(3-(bis(4-methoxybenzyl)amino)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)ureido)-2-phenylacetate

HRID 590885

Reaktionsgleichung

Reaktionsgleichung von HRID 590885
[CH3:1][O:2][C:3]1[CH:48]=[CH:47][C:6]([CH2:7][N:8]([CH2:38][C:39]2[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=2)[C:9]2[C:13]3[CH:14]=[N:15][C:16]([NH2:18])=[CH:17][C:12]=3[N:11]([C:19]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:10]=2)=[CH:5][CH:4]=1.C1N=CN([C:54](N2C=NC=C2)=[O:55])C=1.N1C=CN=C1.CCN(C(C)C)C(C)C.[CH3:75][O:76][C:77](=[O:86])[C@@H:78]([NH2:85])[C:79]1[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=1>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]([CH2:38][C:39]2[CH:40]=[CH:41][C:42]([O:45][CH3:46])=[CH:43][CH:44]=2)[C:9]2[C:13]3[CH:14]=[N:15][C:16]([NH:18][C:54](=[O:55])[NH:85][C@@H:78]([C:79]4[CH:80]=[CH:81][CH:82]=[CH:83][CH:84]=4)[C:77]([O:76][CH3:75])=[O:86])=[CH:17][C:12]=3[N:11]([C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[N:10]=2)=[CH:47][CH:48]=1

Komponenten

7

Edukt 5

HCID 795ImidazoleHCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 1201451Methyl phenylglycinate, L-HCID 1182723773-N,N-bis(4-methoxybenzyl)-1-trityl-1H-pyrazolo[4,3-c]pyridine-3,6-diamine

Produkt 1

HCID 131734504Methyl (S)-2-(3-(3-(bis(4-methoxybenzyl)amino)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)ureido)-2-phenylacetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 3-N,N-bis(4-methoxybenzyl)-1-trityl-1H-pyrazolo[4,3-c]pyridine-3,6-diamine (0.1 g, 0.16 mmol) in anhydrous 1,4-dioxane (3 mL) was added CDI (0.13 g, 0.79 mmol) followed by the addition of imidazole (0.05 g, 0.78 mmol) and the contents were stirred at ambient temperature. After 16 h, DIPEA (0.12 mL, 0.64 mmol) and (S)-methyl-2-amino-2-phenylacetate (0.064 g, 0.32 mmol) were added and stirred. After 2 h, the reaction mixture was quenched with H2O and the organic contents were extracted with EtOAc (2×20 mL), dried over anhydrous Na2SO4 and concentrated. The residue thus obtained was purified by preparative HPLC to afford the title compound MS ES calc'd. for C51H46N6O5 [M+H]+ 823. Found 823.

Aufarbeitung

  1. stirringstirred
  2. waitAfter 2 h
  3. customthe reaction mixture was quenched with H2O
  4. extractionthe organic contents were extracted with EtOAc (2×20 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. customThe residue thus obtained
  8. customwas purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-a1a7e7a2af0941cfbae85fcd17e75210
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09233979B2

Verknüpfte Notizen

Wird geladen…