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Diisopropylethylamine → HCID 11977992, Verbindung

HRID 2241164
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2241164
[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([NH:11][C:12]2[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=2)[C:15]([OH:17])=O)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.C([O:23][C:24](=[O:33])[C:25]1[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][C:26]=1[F:32])C.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(OCC)(=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([NH:11][C:12]2[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=2)[C:15]([NH:31][C:28]2[CH:29]=[CH:30][C:25]([C:24]([OH:33])=[O:23])=[C:26]([F:32])[CH:27]=2)=[O:17])(=[O:9])=[O:10])[CH:5]=[CH:6][CH:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 81531DiisopropylethylamineHCID 8190984Amberlite IR 120 PlusHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10797532Ethyl 4-Amino-2-fluorobenzoate

Produkt 1

HCID 11977992HCID 11977992, VerbindungAusbeute 15,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 3-(3-chloro-benzenesulfonylamino)-benzoic acid (31.1 mg, 0.10 mmol) in DMF (0.5 ml) was added to 4-amino-2-fluoro-benzoic acid ethyl ester (20.1 mg, 0.11 mmol). Diisopropyl-ethyl-amine (0.035 ml) was added, followed by a solution of HATU (57.0 mg, 0.15 mmol) in DMF (0.5 ml). The mixture was shaken at room temperature overnight, then diluted with ethyl acetate (4.0 ml) and water (2.0 ml). The organic phase was separated and evaporated. The residue was dissolved in ethanol (0.60 ml) and treated with 3N KOH (0.40 ml). The mixture was shaken at room temperature overnight, then acidified to pH 2 with 3N HCl. Purification by preparative HPLC (ZORBAX Eclipse XDB-C18, 21.2×50 mm, 5 μm, gradient acetonitrile/water+0.1% formic acid) yielded the title compound (7.0 mg, 15%) as a white solid, MS (ISP): m/e=447.0 (M−H).

Aufarbeitung

  1. customThe organic phase was separated
  2. customevaporated
  3. dissolutionThe residue was dissolved in ethanol (0.60 ml)
  4. additiontreated with 3N KOH (0.40 ml)
  5. stirringThe mixture was shaken at room temperature overnight
  6. customPurification by preparative HPLC (ZORBAX Eclipse XDB-C18, 21.2×50 mm, 5 μm, gradient acetonitrile/water+0.1% formic acid)

Quellen und Nachweise

ORD-Eintrag
ord-f62b3ec66f2c490c8309d37883c9d4e1
Quelldatensatz
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07723538B2

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