Cesium carbonate → methyl 2-[[3,5-bis(trifluoromethyl)benzoyl]amino]-4-[3-[(E)-[4-(trifluoromethyl)phenyl]methylideneamino]oxypropoxy]benzoate

HRID 29683ノート

反応式

HRID 29683 の反応式
[CH3:1][O:2][C:3](=[O:32])[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:31])[C:17]1[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[C:19]([C:27]([F:30])([F:29])[F:28])[CH:18]=1.[F:33][C:34]([F:45])([F:44])[C:35]1[CH:43]=[CH:42][C:38]([CH:39]=[N:40][OH:41])=[CH:37][CH:36]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[CH3:1][O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13][O:41]/[N:40]=[CH:39]/[C:38]2[CH:37]=[CH:36][C:35]([C:34]([F:33])([F:45])[F:44])=[CH:43][CH:42]=2)=[CH:6][C:5]=1[NH:15][C:16](=[O:31])[C:17]1[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[C:19]([C:27]([F:30])([F:29])[F:28])[CH:18]=1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 3056297Benzaldehyde, 4-(trifluoromethyl)-, oximeHCID 865974012-(3,5-Bis-trifluoromethyl-benzoylamino)-4-(3-bromo-propoxy)-benzoic acid methyl ester

生成物 1

HCID 57449660methyl 2-[[3,5-bis(trifluoromethyl)benzoyl]amino]-4-[3-[(E)-[4-(trifluoromethyl)phenyl]methylideneamino]oxypropoxy]benzoate収率 78.6%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

This compound was produced using similar methods as those used in Step 5, example 27, starting with 2-(3,5-bis-trifluoromethyl-benzoylamino)-4-(3-bromo-propoxy)-benzoic acid methyl ester (0.35 g, 0.66 mmol), 4-trifluoromethyl-benzaldehyde oxime (0.13 g, 0.70 mmol) and cesium carbonate (0.86 g, 2.65 mmol) in acetone (25 mL). The crude material was purified by flash chromatography through silica gel using diethyl ether/hexanes (0/100 gradient to 10/90) to give 2-{[3,5-bis(trifluoromethyl)benzoyl]amino}-4-{3-[({(1E)-[4-(trifluoromethyl)phenyl]methylidene}amino)oxy]propoxy}benzoic acid methyl ester (0.33 g, 78%) as a white solid. 1H NMR (500 MHz, DMSO-d6); δ 11.78 (s, 1H), 8.51 (s, 2H), 8.45 (s, 1H), 8.37 (s, 1H), 8.10 (d, 1H), 7.97 (d, 1H), 7.79-7.71 (AA′BB′, 4H), 6.88 (dd, 1H), 4.34 (t, 2H), 4.22 (t, 2H), 3.85 (s, 3H), 2.18 (m, 2H).

後処理

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

出典と根拠

ORDレコード
ord-ee8b90e26e4f472dbba90ebb85905437
出典データセット
uspto-grants-2008_09
特許番号
US07420083B2

反応ノート

読み込み中…