Water → HCID 178501268, Verbindung

HRID 1035743Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1035743
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=2)[CH2:7][CH2:6]1)=[O:4].[F:21][C:22]1[CH:23]=[C:24]([CH:32]=[C:33]([F:35])[CH:34]=1)[CH2:25][C:26]1[S:30][C:29]([NH2:31])=[N:28][N:27]=1.C(N(C(C)C)CC)(C)C.O>CN(C)C=O>[F:35][C:33]1[CH:32]=[C:24]([CH:23]=[C:22]([F:21])[CH:34]=1)[CH2:25][C:26]1[S:30][C:29]([NH:31][C:16]([C:15]2[CH:14]=[CH:13][C:12]([O:11][C@@H:8]3[CH2:7][CH2:6][C@H:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:10][CH2:9]3)=[CH:20][CH:19]=2)=[O:18])=[N:28][N:27]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 667401415-(3,5-Difluorobenzyl)-1,3,4-thiadiazol-2-amineHCID 178501272HCID 178501272, Verbindung

Produkt 1

HCID 178501268HCID 178501268, VerbindungAusbeute 38,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2.2 g of cis-4-(4-methoxycarbonylcyclohexyloxy)benzoic acid (7.91 mmol, 1 eq.) are placed in 30 mL of dimethylformamide at room temperature. 1.98 g of 5-(3,5-difluorobenzyl)[1.3.4]thiadiazol-2-ylamine (8.70 mmol, 1.1 eq.), 4.42 g of bromotris-pyrrolidinophosphonium hexafluorophosphonate (9.49 mmol, 1.2 eq.) and 2.76 mL of diisopropylethylamine (15.81 mmol, 2 eq.) are successively added. The reaction mixture is stirred for 6 days at room temperature, poured into water and extracted with ethyl acetate. The organic phase is washed three times with water and once with brine. The organic phase is concentrated and the residue is chromatographed on silica gel, eluting with a gradient of ethyl acetate in heptane ranging from 7% to 30%. 1.5 g of methyl cis-4-{4-[5-(3,5-difluorobenzyl)[1.3.4]thiadiazol-2-ylcarbamoyl]phenoxy}cyclohexanecarboxylate are obtained.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic phase is washed three times with water
  3. concentrationThe organic phase is concentrated
  4. customthe residue is chromatographed on silica gel
  5. washeluting with a gradient of ethyl acetate in heptane ranging from 7% to 30%

Quellen und Nachweise

ORD-Eintrag
ord-f4185056347f494695c4c9a037c8deb8
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546391B2

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