1-Hydroxybenzotriazole → HCID 86655378, Verbindung

HRID 2190425Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2190425
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]3[CH:13]=[C:14]([CH:28]=[CH:29][CH:30]=3)[C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=3)=[O:16])[CH:8]=[CH:7][C:5]=2[N:6]=1.[O:31]1[CH:35]=[C:34]([C:36](O)=[O:37])[N:33]=[CH:32]1.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)C(C)C)C>CN(C)C=O.O>[F:26][C:24]([F:27])([F:25])[C:21]1[CH:20]=[CH:19][C:18]([NH:17][C:15]([C:14]2[CH:13]=[C:12]([CH:30]=[CH:29][CH:28]=2)[O:11][C:9]2[CH:8]=[CH:7][C:5]3[N:6]=[C:2]([NH:1][C:36]([C:34]4[N:33]=[CH:32][O:31][CH:35]=4)=[O:37])[S:3][C:4]=3[CH:10]=2)=[O:16])=[CH:23][CH:22]=1

Komponenten

8

Edukt 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 142814301,3-Oxazole-4-carboxylic acidHCID 86655374HCID 86655374, Verbindung

Produkt 1

HCID 86655378HCID 86655378, VerbindungAusbeute 34,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 3-[(2-amino-1,3-benzothiazol-6-yl)oxy]-N-[4-(trifluoromethyl)phenyl]benzamide (215 mg, 0.50 mmol) produced in Example A25(v), 1,3-oxazole-4-carboxylic acid (113 mg, 1.00 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (192 mg, 1.00 mmol), 1-hydroxybenzotriazole (135 mg, 1.00 mmol) and N-ethyl-N-isopropylpropane-2-amine (260 mg, 2.0 mmol) in N,N-dimethylformamide (5 mL) was stirred at room temperature for 18 hr. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (eluent:hexane/ethyl acetate=1:1), and triturated with diethyl ether to give the title compound (90 mg, 34%) as a white solid.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel chromatography (eluent:hexane/ethyl acetate=1:1)
  5. customtriturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-1a30f153f3ee4904afefa2f362199060
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324395B2

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