Sulfuric Acid → 3-(3,5-difluorophenyl)-5-methyl-N-(1H-pyrazol-4-ylmethyl)-4,5-dihydro-1,2-oxazole-5-carboxamide

HRID 1522765Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1522765
Cl.[NH:2]1[CH:6]=[C:5]([CH2:7][NH2:8])[CH:4]=[N:3]1.C(N(CC)C(C)C)(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[F:39][C:40]1[CH:41]=[C:42]([C:47]2[CH2:51][C:50]([CH3:55])([C:52](O)=[O:53])[O:49][N:48]=2)[CH:43]=[C:44]([F:46])[CH:45]=1.OS(O)(=O)=O>ClCCl>[F:46][C:44]1[CH:43]=[C:42]([C:47]2[CH2:51][C:50]([CH3:55])([C:52]([NH:8][CH2:7][C:5]3[CH:6]=[N:2][NH:3][CH:4]=3)=[O:53])[O:49][N:48]=2)[CH:41]=[C:40]([F:39])[CH:45]=1

Komponenten

8

Edukt 6

HCID 1118Sulfuric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 57415873(1H-Pyrazol-4-yl)methanamine hydrochlorideHCID 683869243-(3,5-Difluorophenyl)-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylic acid

Produkt 1

HCID 683867093-(3,5-difluorophenyl)-5-methyl-N-(1H-pyrazol-4-ylmethyl)-4,5-dihydro-1,2-oxazole-5-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

1-(1H-Pyrazol-4-yl)methanamine hydrochloride (609 mg, 4.56 mmol), N,N-diisopropylethylamine (1.61 g, 12.44 mmol), HOBt (506 mg, 4.15 mmol) and EDCI (1.59 g, 8.29 mmol) were added to a solution of 3-(3,5-difluorophenyl)-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylic acid (1.00 g, 4.15 mmol) in dichloromethane (30 ml), and the mixture was stirred at RT for 16 h. H2SO4 (0.5M, 10 ml) was then added, and the mixture was diluted with CH2Cl2 (20 ml). The aqueous phase was extracted with CH2Cl2 (2×20 ml), the combined organic phases were washed with saturated NaHCO3 solution (30 ml) and dried over Na2SO4, and the solvent was removed. This gave 1.2 g of 3-(3,5-difluorophenyl)-5-methyl-N-(1H-pyrazol-4-ylmethyl)-4,5-dihydro-1,2-oxazole-5-carboxamide which was used without further purification.

Aufarbeitung

  1. extractionThe aqueous phase was extracted with CH2Cl2 (2×20 ml)
  2. washthe combined organic phases were washed with saturated NaHCO3 solution (30 ml)
  3. dry with materialdried over Na2SO4
  4. customthe solvent was removed
  5. customThis gave 1.2 g of 3-(3,5-difluorophenyl)-5-methyl-N-(1H-pyrazol-4-ylmethyl)-4,5-dihydro-1,2-oxazole-5-carboxamide which was used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-3c291fd07bd9452cb2ceca067255dbbc
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09078442B2

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