Water → tert-butyl N-cyclopropylmethyl-N-[7-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-2-(methoxymethyl)pyrazolo[1,5-a]pyridin-3-yl]carbamate

HRID 347853

Reaktionsgleichung

Reaktionsgleichung von HRID 347853
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][O:10][CH3:11])[CH:6]=[C:5]([O:12][CH3:13])[C:4]=1[C:14]1[N:19]2[N:20]=[C:21]([CH2:31][O:32][CH3:33])[C:22]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[C:18]2[CH:17]=[CH:16][CH:15]=1.[H-].[Na+].Br[CH2:37][CH:38]1[CH2:40][CH2:39]1.O>CN(C)C=O.C(OCC)(=O)C>[CH:38]1([CH2:37][N:23]([C:22]2[C:21]([CH2:31][O:32][CH3:33])=[N:20][N:19]3[C:14]([C:4]4[C:5]([O:12][CH3:13])=[CH:6][C:7]([CH2:9][O:10][CH3:11])=[CH:8][C:3]=4[O:2][CH3:1])=[CH:15][CH:16]=[CH:17][C:18]=23)[C:24](=[O:30])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[CH2:40][CH2:39]1

Komponenten

7

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 21084182tert-Butyl N-[7-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-2-(methoxymethyl)pyrazolo[1,5-a]pyridin-3-yl)carbamate

Produkt 1

HCID 21084194tert-butyl N-cyclopropylmethyl-N-[7-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-2-(methoxymethyl)pyrazolo[1,5-a]pyridin-3-yl]carbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a solution of tert-butyl N-[7-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-2-(methoxymethyl)pyrazolo[1,5-a]pyridin-3-yl]carbamate (170 mg) dissolved in N,N-dimethylformamide (4 mL) was added sodium hydride (60% in oil; 22 mg) and (bromomethyl)cyclopropane (0.043 mL), and the reaction mixture was stirred for 30 minutes at 40° C. Water was added to the obtained reaction mixture, extraction was performed with ethyl acetate and the organic extract was washed with brine. The obtained organic extract was dried over anhydrous magnesium sulfate and filtered, and the solvent was evaporated under reduced pressure to afford a crude product of tert-butyl N-cyclopropylmethyl-N-[7-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-2-(methoxymethyl)pyrazolo[1,5-a]pyridin-3-yl]carbamate.

Aufarbeitung

  1. extractionthe organic extract
  2. washwas washed with brine
  3. extractionThe obtained organic extract
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-27f912d5ba7e4cac9b0a137bbc1acf4c
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176216B2

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