Water → 4-{4-[Bis-(3-cyano-propyl)-sulfamoyl]-4,7-diaza-spiro[2.5]oct-7-yl}-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid tert-butyl ester

HRID 589947Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 589947
[C:1]([O:5][C:6]([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:28])(=[O:27])[NH2:26])[CH2:19][CH2:18]3)[C:11]=2[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:36][CH2:37][CH2:38][C:39]#[N:40].O>CN(C=O)C>[C:1]([O:5][C:6]([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:27])(=[O:28])[N:26]([CH2:12][CH2:11][CH2:10][C:9]#[N:8])[CH2:36][CH2:37][CH2:38][C:39]#[N:40])[CH2:19][CH2:18]3)[C:11]=2[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 214124-BromobutyronitrileHCID 682960294-(4-Sulfamoyl-4,7-diaza-spiro[2.5]oct-7-yl)-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid tert-butyl ester2×

Produkt 1

HCID 682960054-{4-[Bis-(3-cyano-propyl)-sulfamoyl]-4,7-diaza-spiro[2.5]oct-7-yl}-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

4-(4-Sulfamoyl-4,7-diaza-spiro[2.5]oct-7-yl)-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid tert-butyl ester (intermediate 2) (112 mg, 0.27 mmol) was dissolved in dry DMF (2 ml), added K2CO3 (38 mg, 0.27 mmol) and cooled to 0° C. A solution of 4-bromobutyronitrile (40 mg, 0.27 mmol) in dry DMF (0.5 mL) was added and the reaction mixture was stirred at rt for 16 h. The crude mixture was treated with water (10 mL) and extracted with EtOAc (3×10 mL). The combined organic phases were washed with H2O (2×10 mL), brine (2×10 mL), dried over Na2SO4, filtered and concentrated in vacuo. The products were purified by flash chromatography on silica using EtOAc in heptane as eluent.

Aufarbeitung

  1. extractionextracted with EtOAc (3×10 mL)
  2. washThe combined organic phases were washed with H2O (2×10 mL), brine (2×10 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe products were purified by flash chromatography on silica

Quellen und Nachweise

ORD-Eintrag
ord-ab45fd09a9224e2a925495e8c2c90e37
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09233964B2

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