3-Thiophenacetic acid → 1-{4-[4-(2-Phenylethyl)-1,3-thiazol-2-yl]piperidin-1-yl}-2-(thiophen-3-yl)ethanone

HRID 549954Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 549954
[S:1]1[CH:5]=[CH:4][C:3]([CH2:6][C:7]([OH:9])=O)=[CH:2]1.CCN(C(C)C)C(C)C.Cl.[C:20]1([CH2:26][CH2:27][C:28]2[N:29]=[C:30]([CH:33]3[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]3)[S:31][CH:32]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1>ClCCl>[C:20]1([CH2:26][CH2:27][C:28]2[N:29]=[C:30]([CH:33]3[CH2:38][CH2:37][N:36]([C:7](=[O:9])[CH2:6][C:3]4[CH:4]=[CH:5][S:1][CH:2]=4)[CH2:35][CH2:34]3)[S:31][CH:32]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

6

Edukt 4

HCID 234043-Thiophenacetic acidHCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 671568834-[4-(2-Phenylethyl)-1,3-thiazol-2-yl]piperidine hydrochloride

Produkt 1

HCID 671566001-{4-[4-(2-Phenylethyl)-1,3-thiazol-2-yl]piperidin-1-yl}-2-(thiophen-3-yl)ethanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Thiophen-3-ylacetic acid (156 mg) and Hünig base (323 mg) are dissolved in dichloromethane (10 ml) and stirred for 30 min. 4-[4-(2-Phenylethyl)-1,3-thiazol-2-yl]piperidine hydrochloride (II-1, 309 mg), prepared according to Process 1.2, is added, and the mixture is stirred for a further 5 min before bromo-tris-pyrrolidino-phosphonium hexafluorophosphate (599 mg) is added. The reaction mixture is stirred at room temperature overnight. After removal of the solvent under reduced pressure, the residue is purified chromatographically. This gives 1-{4-[4-(2-phenylethyl)-1,3-thiazol-2-yl]piperidin-1-yl}-2-(thiophen-3-yl)ethanone (99 mg).

Aufarbeitung

  1. additionis added
  2. additionis added
  3. stirringThe reaction mixture is stirred at room temperature overnight
  4. customAfter removal of the solvent under reduced pressure
  5. customthe residue is purified chromatographically

Quellen und Nachweise

ORD-Eintrag
ord-67cfe133545b41efb67a8a327724c2a3
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07943774B2

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