Water → methanesulfonic acid 2-methyl-3-[4-(7-methyl-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-pyrazolo[1,5-a]pyridin-5-ylmethyl ester

HRID 402872Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 402872
[CH3:1][S:2]([O:5]S(C)(=O)=O)(=[O:4])=[O:3].O[CH2:11][C:12]1[CH:17]=[CH:16][N:15]2[N:18]=[C:19]([CH3:38])[C:20]([C:21]3[C:22](=[O:37])[NH:23][C:24](=[O:36])[C:25]=3[C:26]3[C:34]4[C:29](=[C:30]([CH3:35])[CH:31]=[CH:32][CH:33]=4)[NH:28][CH:27]=3)=[C:14]2[CH:13]=1.C(N(CC)CC)C.O>C1COCC1>[CH3:38][C:19]1[C:20]([C:21]2[C:22](=[O:37])[NH:23][C:24](=[O:36])[C:25]=2[C:26]2[C:34]3[C:29](=[C:30]([CH3:35])[CH:31]=[CH:32][CH:33]=3)[NH:28][CH:27]=2)=[C:14]2[CH:13]=[C:12]([CH2:11][O:5][S:2]([CH3:1])(=[O:4])=[O:3])[CH:17]=[CH:16][N:15]2[N:18]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 81560Methanesulfonic anhydrideHCID 591920083-(5-hydroxymethyl-2-methyl-pyrazolo[1,5-a]pyridin-3-yl)-4-(7-methyl-1H-indol-3-yl)-pyrrole-2,5-dione

Produkt 1

HCID 59192039methanesulfonic acid 2-methyl-3-[4-(7-methyl-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-pyrazolo[1,5-a]pyridin-5-ylmethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Methanesulfonic anhydride (815 mg, 4.49 mmol, 4.3 equiv) is added at room temperature under an atmosphere of argon to a solution of 3-(5-hydroxymethyl-2-methyl-pyrazolo[1,5-a]pyridin-3-yl)-4-(7-methyl-1H-indol-3-yl)-pyrrole-2,5-dione (400 mg, 1.04 mmol) and of triethyl amine (0.314 ml, 2.25 mmol, 2.2 equiv) in anhydrous THF (10 ml). The reaction mixture is stirred for 1 hour at room temperature. Water is added, and the mixture is extracted three times with EtOAc. The combined organic layers are dried over Na2SO4, filtered, and concentrated in vacuo. The residue (450 mg, 94%) is used directly in the next transformation.

Aufarbeitung

  1. extractionthe mixture is extracted three times with EtOAc
  2. dry with materialThe combined organic layers are dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3ef7ad30ec84484eac45b30dea08e87d
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08742132B2

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