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

HRID 644169

반응식

HRID 644169 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]([F:24])[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].N1C=CC=CC=1.C(Cl)(=O)C(Cl)=O.[Cl:37][C:38]1[CH:39]=[CH:40][C:41]([NH:44][C:45](=[O:53])[C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=2[NH2:52])=[N:42][CH:43]=1>C(Cl)Cl.CN(C=O)C>[F:24][C:22]1[CH:21]=[CH:20][C:16]([C:17]([NH:52][C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][C:46]=2[C:45]([NH:44][C:41]2[CH:40]=[CH:39][C:38]([Cl:37])=[CH:43][N:42]=2)=[O:53])=[O:19])=[C:15]([O:14][CH:11]2[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])[CH2:9][CH2:10]2)[CH:23]=1

참가 물질

7

반응물 4

HCID 1049Pyridine2회HCID 65578Oxalyl chlorideHCID 219063812-amino-N-(5-chloropyridin-2-yl)benzamideHCID 576024392-(1-tert-Butoxycarbonylpiperidin-4-yloxy)-4-fluorobenzoic acid

생성물 1

HCID 685302072-[4-Fluoro-2-(1-tert-butoxycarbonylpiperidin-4-yloxy)benzoylamino]-N-(5-chloropyridin-2-yl)benzamide수율 85%

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매2회

실험 절차

The 2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-fluorobenzoic acid (507 mg, 2.05 mmol) was diluted with methylene chloride (20 mL). DMF (4 drops) and pyridine (0.2 mL, 2.47 mmol) were added, followed by oxalyl chloride (0.2 mL, 2.29 mmol). Vigorous bubbling occurred. After 1.5 hours, the reaction was concentrated in vacuo. The residue was diluted with methylene chloride (20 mL). N-(5-Chloropyridin-2-yl)-2-aminobenzamide (507 mg, 2.05 mmol) was added, followed by pyridine (0.2 mL, 2.47 mmol). After stirring overnight, the reaction was diluted with methylene chloride (100 mL) and washed with water (2×10 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated. The crude residue was purified by flash column chromatography (100% CH2Cl2 to 10% EtOAc/CH2Cl2) to give the desired product (992 mg, 1.74 mmol, 85%) as a white solid.

후처리

  1. customVigorous bubbling
  2. concentrationthe reaction was concentrated in vacuo
  3. additionThe residue was diluted with methylene chloride (20 mL)
  4. washwashed with water (2×10 mL)
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude residue was purified by flash column chromatography (100% CH2Cl2 to 10% EtOAc/CH2Cl2)

출처 및 근거

ORD 기록
ord-43bc4ad42ba94d33bcc9e35c0d537f6e
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07700628B2

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