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Pyridine → 2-[4-(N,N-Dimethylamino)-2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-benzoylamino]-N-(5-chloropyridin-2-yl)benzamide

HRID 644163
ノート
印刷プレビュー

反応式

HRID 644163 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:23]=[C:22]([N:24]([CH3:26])[CH3:25])[CH:21]=[CH:20][C:16]=2[C:17]([OH:19])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:27]1C=CC=CC=1.C(Cl)(=O)C(Cl)=O.[Cl:39][C:40]1[CH:45]=[CH:44][C:43]([NH:46][C:47](=[O:55])[C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=2[NH2:54])=C[CH:41]=1>CN(C=O)C.C(Cl)Cl>[CH3:25][N:24]([C:22]1[CH:21]=[CH:20][C:16]([C:17]([NH:54][C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][C:48]=2[C:47]([NH:46][C:43]2[CH:44]=[CH:45][C:40]([Cl:39])=[CH:41][N:27]=2)=[O:55])=[O:19])=[C:15]([O:14][CH:11]2[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10]2)[CH:23]=1)[CH3:26]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 1049Pyridine2 回HCID 65578Oxalyl chlorideHCID 6704722-amino-N-(4-chlorophenyl)benzamideHCID 576024362-(1-Tert-butoxycarbonylpiperidin-4-yloxy)-4-(dimethyl-amino)benzoic acid

生成物 1

HCID 685339532-[4-(N,N-Dimethylamino)-2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-benzoylamino]-N-(5-chloropyridin-2-yl)benzamide収率 85.1%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a mixture of 2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-(N,N-dimethyl-amino)benzoic acid (950 mg, 2.61 mmol), pyridine (0.23 mL, 2.86 mmol), DMF (1 drop) and methylene chloride (15 mL) was added oxalyl chloride (0.24 mL, 2.73 mmol) dropwise. After 15 minutes, more pyridine (0.23 mL, 2.86 mmol) was added, followed by the N-(4-chlorophenyl)-2-aminobenzamide (645 mg, 2.61 mmol). The reaction was stirred for 1 hour, diluted with methylene chloride, washed with 50% saturated aqueous sodium bicarbonate, and dried over Na2 SO4. The organic solution was concentrated, chromatographed (2000 g silica, 5% EtOAc/CH2Cl2 to 15% EtOAc/CH2Cl2), and triturated with ether to give the desired product (1.32 g, 83%).

後処理

  1. washwashed with 50% saturated aqueous sodium bicarbonate
  2. customdried over Na2 SO4
  3. concentrationThe organic solution was concentrated
  4. customchromatographed (2000 g silica, 5% EtOAc/CH2Cl2 to 15% EtOAc/CH2Cl2)
  5. customtriturated with ether

出典と根拠

ORDレコード
ord-9c2ba8cbeef64b989a018083472f5c02
出典データセット
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07700628B2

反応ノート

読み込み中…

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