2-Fluoroethylamine → 3-[5-(3,5-Dichloro-4-fluoro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carboxylic acid [(2-fluoro-ethylcarbamoyl)-methyl]-amide

HRID 240907

Reaktionsgleichung

Reaktionsgleichung von HRID 240907
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2([C:30]([F:33])([F:32])[F:31])[O:14][N:13]=[C:12]([C:15]3[S:19][C:18]([C:20]([NH:22][CH2:23][C:24]([OH:26])=O)=[O:21])=[C:17]4[CH2:27][CH2:28][CH2:29][C:16]=34)[CH2:11]2)[CH:5]=[C:6]([Cl:9])[C:7]=1[F:8].C(N(CC)C(C)C)(C)C.[F:43][CH2:44][CH2:45][NH2:46].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(#N)C>[F:43][CH2:44][CH2:45][NH:46][C:24]([CH2:23][NH:22][C:20]([C:18]1[S:19][C:15]([C:12]2[CH2:11][C:10]([C:4]3[CH:5]=[C:6]([Cl:9])[C:7]([F:8])=[C:2]([Cl:1])[CH:3]=3)([C:30]([F:31])([F:32])[F:33])[O:14][N:13]=2)=[C:16]2[CH2:29][CH2:28][CH2:27][C:17]=12)=[O:21])=[O:26]

Komponenten

6

Edukt 4

HCID 99962-FluoroethylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86693752({3-[5-(3,5-Dichloro-4-fluoro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carbonyl}-amino)-acetic acid

Produkt 1

HCID 714725683-[5-(3,5-Dichloro-4-fluoro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carboxylic acid [(2-fluoro-ethylcarbamoyl)-methyl]-amideAusbeute 92,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of compound ({3-[5-(3,5-Dichloro-4-fluoro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carbonyl}-amino)-acetic acid (100 mg, 0.19 mmol) in acetonitrile (5 mL) is added N,N-diisopropylethylamine (49.3 mg, 0.38 mmol), 2-fluoro-ethylamine (14.4 mg, 0.23 mmol) and HATU (108.8 mg, 0.29 mmol), after finished the mixture is stirred at room temperature for 1 hour. After being detected by TLC and LCMS, the reaction mixture is concentrated and the residue is purified by column chromatography to afford desired product (100 mg, 92%). MS (m/z): 570.1 (M+1).

Aufarbeitung

  1. concentrationthe reaction mixture is concentrated
  2. customthe residue is purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8b7a4a6d2f40424193e6636c5833429d
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08648081B2

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