Bis(2-oxo-3-oxazolidinyl)phosphinic chloride → 1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-5-(1-isopropyl-piperidin-4-ylcarbamoyl)-1H-pyrazole-3-carboxylic acid methyl ester

HRID 33244

Reaktionsgleichung

Reaktionsgleichung von HRID 33244
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([C:10](O)=[O:11])[N:7]([CH2:13][C:14]2[CH:18]=[C:17]([C:19]3[S:20][C:21]([Cl:24])=[CH:22][CH:23]=3)[O:16][N:15]=2)[N:6]=1)=[O:4].C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.Cl.[CH:41]([N:44]1[CH2:49][CH2:48][CH:47]([NH2:50])[CH2:46][CH2:45]1)([CH3:43])[CH3:42]>C(Cl)Cl.CCN(CC)CC>[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([C:10](=[O:11])[NH:50][CH:47]2[CH2:48][CH2:49][N:44]([CH:41]([CH3:43])[CH3:42])[CH2:45][CH2:46]2)[N:7]([CH2:13][C:14]2[CH:18]=[C:17]([C:19]3[S:20][C:21]([Cl:24])=[CH:22][CH:23]=3)[O:16][N:15]=2)[N:6]=1)=[O:4]

Komponenten

6

Edukt 3

HCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 230334601-Isopropylpiperidin-4-amine hydrochlorideHCID 602079521-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-1H-pyrazole-3,5-dicarboxylic acid 3-methyl ester

Produkt 1

HCID 104357451-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-5-(1-isopropyl-piperidin-4-ylcarbamoyl)-1H-pyrazole-3-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To 1 g 1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-1H-pyrazole-3,5-dicarboxylic acid 3-methyl ester in 10 ml DCM and 1.4 ml NEt3, 667 mg BOP-Cl were added at RT and the mixture was stirred for 30 min. After addition of 563 mg 1-Isopropyl-piperidin-4-ylamine hydrochloride the mixture was stirred for 16 h. After removal of the solvent under reduced pressure the residue was purified by silica gel chromatography eluting with DCM/MeOH/AcOH/H2O 20:10:1:1 to yield a white solid. Yield: 800 mg MS (ES+): m/e=492, chloro pattern.

Aufarbeitung

  1. stirringwas stirred for 16 h
  2. customAfter removal of the solvent under reduced pressure the residue
  3. customwas purified by silica gel chromatography
  4. washeluting with DCM/MeOH/AcOH/H2O 20:10:1:1
  5. customto yield a white solid

Quellen und Nachweise

ORD-Eintrag
ord-772a0e79d491429d936dd965d3cf8e88
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07429581B2

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