Water → {Methyl-[7-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diaza-spiro[2.5]octane-4-sulfonyl]-amino}-acetic acid methyl ester

HRID 589966Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 589966
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+].[CH3:36][O:37][C:38](=[O:41])[CH2:39]Cl.O>CN(C=O)C>[CH3:36][O:37][C:38](=[O:41])[CH2:39][N:26]([CH3:27])[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:28])=[O:29]

Komponenten

6

Edukt 4

HCID 962WaterHCID 7295Methyl chloroacetateHCID 10796Cesium carbonateHCID 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 57410569{Methyl-[7-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diaza-spiro[2.5]octane-4-sulfonyl]-amino}-acetic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
40 °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) (0.047 mmol) was dissolved in dry DMF (0.5 mL) and added Cs2CO3 (0.071 mmol) and chloro-acetic acid methyl ester (0.071 mmol). Stirred at 40° C. for 2 h and then added H2O (1.5 mL). Extracted with EtOAc (3×1 mL) and the combined organic phases were washed with brine (1 mL) and concentrated in vacuo. The residual oil was treated with TFA (1 mL) at rt for 1 h. The crude reaction mixture was concentrated in vacuo and redissolved in DMSO (0.5 mL). The pure compound was obtained by standard preparative HPLC purification of the reaction mixture.

Aufarbeitung

  1. extractionExtracted with EtOAc (3×1 mL)
  2. washthe combined organic phases were washed with brine (1 mL)
  3. concentrationconcentrated in vacuo
  4. additionThe residual oil was treated with TFA (1 mL) at rt for 1 h
  5. customThe crude reaction mixture
  6. concentrationwas concentrated in vacuo
  7. dissolutionredissolved in DMSO (0.5 mL)
  8. customThe pure compound was obtained by standard preparative HPLC purification of the reaction mixture

Quellen und Nachweise

ORD-Eintrag
ord-0f4a5bbf95aa4293b71f4ae633e5df0d
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09233964B2

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