Trimethylsilyl iodide → 2-(4-tert-Butylphenoxy)-N-{2-(5-chloro-8-hydroxyquinolin-7-yl)-1-[3-(5-methyl-2-thienyl)phenyl]ethyl}acetamide

HRID 551134노트

반응식

HRID 551134 반응식
[CH2:1]([O:8][C:9]1[C:10]([CH2:20][CH:21]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]3[S:30][C:31]([CH3:34])=[CH:32][CH:33]=3)[CH:24]=2)[NH2:22])=[CH:11][C:12]([Cl:19])=[C:13]2[C:18]=1[N:17]=[CH:16][CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:35]([C:39]1[CH:49]=[CH:48][C:42]([O:43][CH2:44][C:45](Cl)=[O:46])=[CH:41][CH:40]=1)([CH3:38])([CH3:37])[CH3:36].[Si](I)(C)(C)C>C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[C:10]([CH2:20][CH:21]([NH:22][C:45](=[O:46])[CH2:44][O:43][C:42]2[CH:48]=[CH:49][C:39]([C:35]([CH3:37])([CH3:36])[CH3:38])=[CH:40][CH:41]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]3[S:30][C:31]([CH3:34])=[CH:32][CH:33]=3)[CH:24]=2)=[CH:11][C:12]([Cl:19])=[C:13]2[C:18]=1[N:17]=[CH:16][CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:35]([C:39]1[CH:49]=[CH:48][C:42]([O:43][CH2:44][C:45]([NH:22][CH:21]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]3[S:30][C:31]([CH3:34])=[CH:32][CH:33]=3)[CH:24]=2)[CH2:20][C:10]2[C:9]([OH:8])=[C:18]3[C:13]([CH:14]=[CH:15][CH:16]=[N:17]3)=[C:12]([Cl:19])[CH:11]=2)=[O:46])=[CH:41][CH:40]=1)([CH3:38])([CH3:36])[CH3:37]

참가 물질

6

반응물 3

HCID 85247Trimethylsilyl iodideHCID 6111954-tert-Butylphenoxyacetyl chlorideHCID 67171449HCID 67171449, 화합물

생성물 2

HCID 598296952-(4-tert-Butylphenoxy)-N-{2-(5-chloro-8-hydroxyquinolin-7-yl)-1-[3-(5-methyl-2-thienyl)phenyl]ethyl}acetamide수율 126.6%HCID 67171827N-{2-(8-Benzyloxy-5-chloro-quinolin-7-yl)-1-[3-(5-methyl-thiophen-2-yl)-phenyl]-ethyl}-2-(4-tert-butyl-phenoxy)-acetamide

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

N-{2-(8-Benzyloxy-5-chloro-quinolin-7-yl)-1-[3-(5-methyl-thiophen-2-yl)-phenyl]-ethyl}-2-(4-tert-butyl-phenoxy)-acetamide was prepared from 2-[8-(benzyloxy)-5-chloroquinolin-7-yl]-1-[3-(5-methyl-2-thienyl)phenyl]ethanamine (0.414 mmol) and 4-tert-butyl-phenoxyacetyl chloride (0.455 mmol, 1.1 eq.) according to the general procedure described above (Alternate General Procedure for N-Acylations). Ethyl acetate was used in place of dichloromethane in the workup procedure. Crude product obtained was a white solid that was subjected to the conditions described above for TMSI-mediated O-benzyl deprotection Crude product obtained was a brown solid that was purified by column chromatography using 5% methanol/dichloromethane to give the title compound as a white solid (0.262 mmol, 64% for 2 steps). MS (ESI) m/z 585.4.

후처리

  1. customCrude product obtained
  2. customobtained
  3. customwas purified by column chromatography

출처 및 근거

ORD 기록
ord-b8e803d0fa9e4a21a509e24b2507dc6e
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07947712B2

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