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Triethylamine → HCID 11613519, 화합물

HRID 1367705
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HRID 1367705 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[N:11]([C:20](Cl)=[O:21])[C:10]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[O:29][CH2:30][CH3:31])=[N:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[NH:39]1[CH2:44][CH2:43][NH:42][CH2:41][C:40]1=[O:45].C(OCC)(=O)C>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[N:11]([C:20]([N:42]3[CH2:43][CH2:44][NH:39][C:40](=[O:45])[CH2:41]3)=[O:21])[C:10]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[O:29][CH2:30][CH3:31])=[N:9]2)=[CH:6][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 231360Piperazin-2-oneHCID 11561933HCID 11561933, 화합물

생성물 1

HCID 11613519HCID 11613519, 화합물수율 60.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (4S,5R)-4,5-bis-(4-chloro-phenyl)-2-(2-ethoxy-phenyl)-4,5-dihydro-imidazole-1-carbonyl chloride (100 mg, 0.211 mmol, example 7) in methylene chloride (3 mL) cooled to 0° C. were added triethylamine (30 uL, 0.211 mmol) and 2-piperazinone (23 mg, 0.232 mmol), respectively. After 15 min, thin layer chromatography (silica gel, 20% ethyl acetate in hexanes) showed no starting material left. The reaction mixture was loaded into a flash silica gel column (12 g). Purification by flash column chromatography (eluting with 5% methanol and 0.1% triethylamine in ethyl acetate using Intelliflash 280 system) gave 4-[(4S,5R)-4,5-bis-(4-chloro-phenyl)-2-(2-ethoxy-phenyl)-4,5-dihydro-imidazole-1-carbonyl]-piperazin-2-one as a white foam (69 mg). HR-MS (ES, m/z) calculated for C30H31N4O4Cl2 [(M+H)+] 581.1717, observed 581.1717

후처리

  1. waitleft
  2. customPurification
  3. washby flash column chromatography (eluting with 5% methanol and 0.1% triethylamine in ethyl acetate using Intelliflash 280 system)

출처 및 근거

ORD 기록
ord-611f0314e9d14357aaea0256c5b8302a
출처 데이터셋
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07893278B2

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