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

HRID 644169

反応式

HRID 644169 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]([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

参加物

7

反応物 4

HCID 1049Pyridine2 回HCID 65578Oxalyl chlorideHCID 219063812-amino-N-(5-chloropyridin-2-yl)benzamideHCID 576024392-(1-tert-Butoxycarbonylpiperidin-4-yloxy)-4-fluorobenzoic acid

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-43bc4ad42ba94d33bcc9e35c0d537f6e
出典データセット
uspto-grants-2010_04
特許番号
US07700628B2

関連ノート

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