3-(4-Tert-butylphenyl)-5-(chloromethyl)-1,2,4-oxadiazole → (R)-1-{4-[3-(4-tert-Butyl-phenyl)-[1,2,4]oxadiazol-5-ylmethyl]-piperazin-1-yl}-3-(2-methyl-benzothiazol-5-yloxy)-propan-2-ol

HRID 1827878Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1827878
[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([O:11][CH2:12][C@H:13]([OH:21])[CH2:14][N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)=[CH:7][C:5]=2[N:6]=1.[C:22]([C:26]1[CH:31]=[CH:30][C:29]([C:32]2[N:36]=[C:35]([CH2:37]Cl)[O:34][N:33]=2)=[CH:28][CH:27]=1)([CH3:25])([CH3:24])[CH3:23]>CN(C)C.C(O)C>[C:22]([C:26]1[CH:27]=[CH:28][C:29]([C:32]2[N:36]=[C:35]([CH2:37][N:18]3[CH2:17][CH2:16][N:15]([CH2:14][C@@H:13]([OH:21])[CH2:12][O:11][C:8]4[CH:9]=[CH:10][C:4]5[S:3][C:2]([CH3:1])=[N:6][C:5]=5[CH:7]=4)[CH2:20][CH2:19]3)[O:34][N:33]=2)=[CH:30][CH:31]=1)([CH3:25])([CH3:24])[CH3:23]

Komponenten

4

Edukt 2

HCID 27817013-(4-Tert-butylphenyl)-5-(chloromethyl)-1,2,4-oxadiazoleHCID 29943216(2R)-1-(2-methylbenzothiazol-5-yloxy)-3-piperazinylpropan-2-ol

Produkt 1

HCID 9984207(R)-1-{4-[3-(4-tert-Butyl-phenyl)-[1,2,4]oxadiazol-5-ylmethyl]-piperazin-1-yl}-3-(2-methyl-benzothiazol-5-yloxy)-propan-2-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 86589564Trimethylamine ethanolLösungsmittel

Versuchsvorschrift

A solution of (2R)-1-(2-methylbenzothiazol-5-yloxy)-3-piperazinylpropan-2-ol, a compound of formula (6) (75 mg, 0.14 mmol), and 3-(4-tert-butylphenyl)-5-chloromethyl-1,2,4-oxadiazole (40 mg, 0.16 mmol) in 10% trimethylamine/ethanol, was heated to 73° C. and allowed to stir overnight. The solvent was evaporated under reduced pressure, and the resulting residue chromatographed by preparative thin layer chromatography (PTLC) (3% methanol/methylene chloride). The resulting oil was diluted with methylene chloride and placed on the high Vac. overnight, to yield (2R)-3-[4-({3-[4-(tert-butyl)phenyl](1,2,4-oxadiazol-5-yl)}methyl)piperazinyl]-1-(2-methylbenzothiazol-5-yloxy)propan-2-ol as a white solid.

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure
  2. customthe resulting residue chromatographed by preparative thin layer chromatography (PTLC) (3% methanol/methylene chloride)
  3. additionThe resulting oil was diluted with methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-2682298f29854c30a55d1242c156871d
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07056924B2

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