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4-Fluorobenzyl chloride → 3-Cyano-1-(4-fluoro-benzyl)-6-hydroxy-7-oxo-1,7-dihydro-pyrazolo[1,5-a]pyrimidine-5-carboxylic acid 4-fluoro-benzylamide

HRID 1097745
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1097745
[H-].[Na+].[F:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8]N)=[CH:6][CH:5]=1.[F:12][C:13]1[CH:35]=[CH:34][C:16]([CH2:17][NH:18][C:19]([C:21]2[N:22]=[C:23]3[C:31]([C:32]#[N:33])=[CH:30][NH:29][N:24]3[C:25](=[O:28])[C:26]=2[OH:27])=[O:20])=[CH:15][CH:14]=1.FC1C=CC(CCl)=CC=1>CN(C=O)C>[F:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:17][NH:18][C:19]([C:21]2[N:22]=[C:23]3[C:31]([C:32]#[N:33])=[CH:30][N:29]([CH2:8][C:7]4[CH:10]=[CH:11][C:4]([F:3])=[CH:5][CH:6]=4)[N:24]3[C:25](=[O:28])[C:26]=2[OH:27])=[O:20])=[CH:34][CH:35]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 96024-Fluorobenzyl chlorideHCID 24758Sodium hydrideHCID 866430543-cyano-N-[(4-fluorophenyl)methyl]-6-hydroxy-7-oxo-1H-pyrazolo[1,5-a]pyrimidine-5-carboxamide;(4-fluorophenyl)methanamine

Produkt 1

HCID 668103533-Cyano-1-(4-fluoro-benzyl)-6-hydroxy-7-oxo-1,7-dihydro-pyrazolo[1,5-a]pyrimidine-5-carboxylic acid 4-fluoro-benzylamideAusbeute 37,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Sodium hydride (11.0 mg, 0.367 mmol) was added in one portion to a stirred suspension of 3-Cyano-6-hydroxy-7-oxo-1,7-dihydro-pyrazolo[1,5-a]pyrimidine-5-carboxylic acid 4-fluoro-benzylamide compound with 4-fluorobenzylamine (Example 3.1) (100 mg, 0.306 mmol) in DMF (2 mL) under nitrogen at room temperature. The mixture was stirred for 30 min before p-fluorobenzyl chloride (40 μL, 0.366 mmol) was added and the mixture heated at 90° C. for 2 days. After this time, the reaction was cooled to room temperature and partitioned between ethyl acetate (10 mL) and aqueous hydrochloric acid (1M, 10 mL). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (3×10 mL). The combined organics were washed with water (3×10 mL), brine (10 mL) and then concentrated. The residue was purified by column chromatography (95:5:1 dichloromethane:methanol:aqueous ammonia) to afford the desired product (50 mg, 36%).

Aufarbeitung

  1. additionwas added
  2. temperatureAfter this time, the reaction was cooled to room temperature
  3. custompartitioned between ethyl acetate (10 mL) and aqueous hydrochloric acid (1M, 10 mL)
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate (3×10 mL)
  6. washThe combined organics were washed with water (3×10 mL), brine (10 mL)
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography (95:5:1 dichloromethane:methanol:aqueous ammonia)

Quellen und Nachweise

ORD-Eintrag
ord-19b2a80a6b79462c8bc7bc42ba5ba0fd
Quelldatensatz
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08143268B2

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