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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
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HRID 644163 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 1049Pyridine2회HCID 65578Oxalyl chlorideHCID 6704722-amino-N-(4-chlorophenyl)benzamideHCID 576024362-(1-Tert-butoxycarbonylpiperidin-4-yloxy)-4-(dimethyl-amino)benzoic acid

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매2회

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-9c2ba8cbeef64b989a018083472f5c02
출처 데이터셋
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07700628B2

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