Water → 7-(7H-Pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diaza-spiro[2.5]octane-4-sulfonic acid methyl-(3-phenyl-propyl)-amide

HRID 589965Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 589965
C(OC([N:8]1[C:12]2[N:13]=[CH:14][N:15]=[C:16]([N:17]3[CH2:24][C:21]4([CH2:23][CH2:22]4)[N:20]([S:25](=[O:29])(=[O:28])[NH:26][CH3:27])[CH2:19][CH2:18]3)[C:11]=2[CH:10]=[CH:9]1)=O)(C)(C)C.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:37][CH2:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.O>CN(C=O)C>[CH3:27][N:26]([CH2:37][CH2:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[S:25]([N:20]1[CH2:19][CH2:18][N:17]([C:16]2[C:11]3[CH:10]=[CH:9][NH:8][C:12]=3[N:13]=[CH:14][N:15]=2)[CH2:24][C:21]21[CH2:22][CH2:23]2)(=[O:29])=[O:28]

Komponenten

6

Edukt 4

HCID 962WaterHCID 10796Cesium carbonateHCID 12503(3-Bromopropyl)benzeneHCID 682959194-(4-Methylsulfamoyl-4,7-diaza-spiro[2.5]oct-7-yl)-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid tert-butyl ester2×

Produkt 1

HCID 682960107-(7H-Pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diaza-spiro[2.5]octane-4-sulfonic acid methyl-(3-phenyl-propyl)-amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
35 °C

Versuchsvorschrift

4-(4-Methylsulfamoyl-4,7-diaza-spiro[2.5]oct-7-yl)-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid tert-butyl ester (intermediate 4) (0.71 mmol) was dissolved in dry DMF (0.5 mL) and added Cs2CO3 (0.85 mmol) and (3-bromo-propyl)-benzene (0.085 mmol). Stirred at 35° C. for 1.5 h and then added H2O (2 mL). Extracted with EtOAc (3×2 mL) and the combined organic phases were concentrated in vacuo. The residual oil was treated with TFA (2 mL) at rt→45° C. for 1.5 h. The crude reaction mixture was concentrated in vacuo and redissolved in DMSO (0.5 mL). The pure compounds were obtained by standard preparative HPLC purification of the reaction mixture.

Aufarbeitung

  1. extractionExtracted with EtOAc (3×2 mL)
  2. concentrationthe combined organic phases were concentrated in vacuo
  3. additionThe residual oil was treated with TFA (2 mL) at rt→45° C. for 1.5 h
  4. customThe crude reaction mixture
  5. concentrationwas concentrated in vacuo
  6. dissolutionredissolved in DMSO (0.5 mL)
  7. customThe pure compounds were obtained by standard preparative HPLC purification of the reaction mixture

Quellen und Nachweise

ORD-Eintrag
ord-06f5e679552a426cbdcb6ab3f6925d09
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09233964B2

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