Triethylamine → N-{4-[4-(2-methyl-allyl)-piperazin-1-yl]-phenyl}-2-oxo-2-(2-phenyl-5,6,7,8-tetrahydro-indolizin-3-yl)-acetamide

HRID 37876노트

반응식

HRID 37876 반응식
[CH3:1][C:2](=[CH2:17])[CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1.C(N(CC)CC)C.[O:25]=[C:26]([C:30]1[N:38]2[C:33]([CH2:34][CH2:35][CH2:36][CH2:37]2)=[CH:32][C:31]=1[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:27](Cl)=[O:28]>C(Cl)Cl>[CH3:17][C:2](=[CH2:1])[CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:27](=[O:28])[C:26](=[O:25])[C:30]3[N:38]4[C:33]([CH2:34][CH2:35][CH2:36][CH2:37]4)=[CH:32][C:31]=3[C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 668514031-(2-Methyl-allyl)-4-(4-amino-phenyl)-piperazineHCID 86649692Oxo-(2-phenyl-5,6,7,8-tetrahydro-indolizin-3-yl)-acetyl chloride

생성물 1

HCID 25095423N-{4-[4-(2-methyl-allyl)-piperazin-1-yl]-phenyl}-2-oxo-2-(2-phenyl-5,6,7,8-tetrahydro-indolizin-3-yl)-acetamide수율 21.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

To an ice-cold solution of 4-[4-(2-methyl-allyl)-piperazin-1-yl]-phenylamine (prepared as described in Reference Example 89, 500 mg, 2.16 mmol) and triethylamine (0.6 mL, 4.32 mmol) in dry DCM (12 mL) was added a solution of oxo-(2-phenyl-5,6,7,8-tetrahydro-indolizin-3-yl)-acetyl chloride (prepared as described in Reference Example 21, 726 mg, 2.52 mmol) in DCM (5 mL). The mixture was warmed to room temperature and stirred for 30 min then diluted with DCM, washed successively with water, sodium bicarbonate solution and brine, then dried over sodium sulfate. Concentration gave a residue which was purified by preparative TLC using ethyl acetate and hexane (3:7) as eluent to afford N-{4-[4-(2-methyl-allyl)-piperazin-1-yl]-phenyl}-2-oxo-2-(2-phenyl-5,6,7,8-tetrahydro-indolizin-3-yl)-acetamide (220 mg, 21%) as a yellow powder.

후처리

  1. washwashed successively with water, sodium bicarbonate solution and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationConcentration
  4. customgave a residue which
  5. customwas purified by preparative TLC

출처 및 근거

ORD 기록
ord-8d62af025a17413e989bdbfd447899f0
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524705B2

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