Triethylamine → Methanesulfonic acid 2-[3-tert-butyl-5-(3-{4-[7-(4-methanesulfonyl-phenyl)-imidazo[1,2-a]pyridin-3-yl]-benzyl}-ureido)-pyrazol-1-yl]-ethyl ester

HRID 1446733Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1446733
[C:1]([C:5]1[CH:6]=[C:7]([NH:13][C:14]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[N:28]4[CH:29]=[CH:30][C:31]([C:33]5[CH:38]=[CH:37][C:36]([S:39]([CH3:42])(=[O:41])=[O:40])=[CH:35][CH:34]=5)=[CH:32][C:27]4=[N:26][CH:25]=3)=[CH:20][CH:19]=2)=[O:15])[N:8]([CH2:10][CH2:11][OH:12])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:50][S:51](Cl)(=[O:53])=[O:52]>C(Cl)Cl>[C:1]([C:5]1[CH:6]=[C:7]([NH:13][C:14]([NH:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]([C:24]3[N:28]4[CH:29]=[CH:30][C:31]([C:33]5[CH:34]=[CH:35][C:36]([S:39]([CH3:42])(=[O:40])=[O:41])=[CH:37][CH:38]=5)=[CH:32][C:27]4=[N:26][CH:25]=3)=[CH:22][CH:23]=2)=[O:15])[N:8]([CH2:10][CH2:11][O:12][S:51]([CH3:50])(=[O:53])=[O:52])[N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 578634381-[5-tert-Butyl-2-(2-hydroxy-ethyl)-2H-pyrazol-3-yl]-3-{4-[7-(4-methanesulfonyl-phenyl)-imidazo[1,2-a]pyridin-3-yl]-benzyl}-urea

Produkt 1

HCID 86634307Methanesulfonic acid 2-[3-tert-butyl-5-(3-{4-[7-(4-methanesulfonyl-phenyl)-imidazo[1,2-a]pyridin-3-yl]-benzyl}-ureido)-pyrazol-1-yl]-ethyl esterAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

In a round bottomed flask dissolve 1-[5-tert-butyl-2-(2-hydroxy-ethyl)-2H-pyrazol-3-yl]-3-{4-[7-(4-methanesulfonyl-phenyl)-imidazo[1,2-a]pyridin-3-yl]-benzyl}-urea (0.2 g, 0.34 mmol) and triethyl amine (0.48 mL, 10 equiv.) in DCM (20 mL) under N2. Add methanesulfonyl chloride (0.13 mL, 4.8 equiv.) dropwise and stir the reaction at room temperature for 15 minutes. Load the crude reaction directly onto silica gel and purify (EtOAc to 5% MeOH: DCM) to give a yellow solid (0.22 g, 97%). MS (ES), m/z 665 (M+1).

Aufarbeitung

  1. customthe reaction at room temperature for 15 minutes
  2. customLoad the crude reaction directly onto silica gel
  3. custompurify (EtOAc to 5% MeOH: DCM)

Quellen und Nachweise

ORD-Eintrag
ord-b46eba72813e4e8fb381fbd57062fd43
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07666879B2

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