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Cesium carbonate → methyl 4-[3-[(E)-(4-phenylphenyl)methylideneamino]oxypropoxy]-2-[[4-(trifluoromethoxy)benzoyl]amino]benzoate

HRID 29677
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HRID 29677 반응식
[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13]Br)=[CH:6][C:5]=1[NH:15][C:16](=[O:28])[C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=1.[C:30]1([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:35]=[CH:34][C:33]([CH:36]=[N:37][OH:38])=[CH:32][CH:31]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13][O:38]/[N:37]=[CH:36]/[C:33]2[CH:34]=[CH:35][C:30]([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)=[CH:31][CH:32]=2)=[CH:6][C:5]=1[NH:15][C:16](=[O:28])[C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 2615464-PhenylbenzaldoximeHCID 692101914-(3-Bromo-propoxy)-2-(4-trifluoromethoxy-benzoylamino)-benzoic acid methyl ester

생성물 1

HCID 87735102methyl 4-[3-[(E)-(4-phenylphenyl)methylideneamino]oxypropoxy]-2-[[4-(trifluoromethoxy)benzoyl]amino]benzoate수율 80%

시약·촉매·용매 1

HCID 180
Acetone
용매

실험 절차

This compound was produced using similar methods as those used in Step 5, example 27, starting with 4-(3-bromo-propoxy)-2-(4-trifluoromethoxy-benzoylamino)-benzoic acid methyl ester (0.46 g, 0.97 mmol), biphenyl-4-carbaldehyde oxime (0.20 g, 1.01 mmol) and cesium carbonate (1.26 g, 3.86 mmol) in acetone (35 mL). The crude material was purified by flash chromatography through silica gel using diethyl ether/hexanes (0/100 gradient to 12/88) to give 4-[3-({[(1E)-1,1′-biphenyl-4-ylmethylidene]amino}oxy)propoxy]-2-{[4-(trifluoromethoxy)benzoyl]amino}benzoic acid methyl ester (0.46 g, 80%) as a white solid. 1H NMR (500 MHz, DMSO-d6); δ 11.93 (s, 1H), 8.34 (d, 1H), 8.31 (s, 1H), 8.06 (d, 2H), 7.99 (d, 1H), 7.70-7.66 (m, 6H), 7.60 (d, 1H), 7.46 (t, 2H), 7.38 (t, 1H), 6.85 (dd, 1H), 4.31 (t, 2H), 4.23 (t, 2H), 3.87 (s, 3H), 2.18 (m, 2H).

후처리

  1. customThis compound was produced
  2. customThe crude material was purified by flash chromatography through silica gel

출처 및 근거

ORD 기록
ord-7ad0965e86ef4bfb8e4dc21023266aaf
출처 데이터셋
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07420083B2

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