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

HRID 549954노트

반응식

HRID 549954 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-67cfe133545b41efb67a8a327724c2a3
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07943774B2

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