Diisopropylethylamine → 5-bromo-N-(5-(4-methoxyphenyl)-1H-pyrazol-3-yl)pentanamide

HRID 1695203Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1695203
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6](Cl)=[O:7].[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[NH:21][N:20]=[C:19]([NH2:22])[CH:18]=2)=[CH:13][CH:12]=1.C(N(C(C)C)CC)(C)C>CC(N(C)C)=O>[CH3:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[NH:21][N:20]=[C:19]([NH:22][C:6](=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2][Br:1])[CH:18]=2)=[CH:15][CH:16]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 5211735-Bromovaleryl chlorideHCID 27564693-Amino-5-(4-methoxyphenyl)pyrazole

Produkt 1

HCID 577800445-bromo-N-(5-(4-methoxyphenyl)-1H-pyrazol-3-yl)pentanamideAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel2×

Versuchsvorschrift

A solution of 5-bromovaleryl chloride (2.1 mL, 15.7 mmol, 1 eq) in dry DMA (35 mL) was cooled to −10° C. (ice/water bath) under N2; a solution of 5-(4-methoxy-phenyl)-1H-pyrazol-3-ylamine (3.0 g, 15.7 mmol, 1 eq) and diisopropylethylamine (2.74 mL, 15.7 mmol, 1 eq) in dry DMA (15 mL) was added over 30 min. After 2 hrs at −10° C., LC-MS shows completion of the reaction which was quenched by addition of H2O (ca. 50 mL). The solid which precipitates was filtered and washed with Et2O, to give 4.68 g of 5-bromo-pentanoic acid [5-(4-methoxy-phenyl)-1H-pyrazol-3-yl]-amide as a white powder (13.3 mmol, 85% yield).

Aufarbeitung

  1. customcompletion of the reaction which
  2. customwas quenched by addition of H2O (ca. 50 mL)
  3. customThe solid which precipitates
  4. filtrationwas filtered
  5. washwashed with Et2O

Quellen und Nachweise

ORD-Eintrag
ord-694a8c96c0714925a961e4c66ea3705b
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163729B2

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