Acetic Acid → N-(5-chloropyridin-2-yl)-5-iodo-2-[(1-isopropylpiperidin-4-ylcarbonyl)amino]benzamide

HRID 1247141ノート

反応式

HRID 1247141 の反応式
F[C:2](F)(F)[C:3](O)=O.[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:16](=[O:33])[C:17]2[CH:22]=[C:21]([I:23])[CH:20]=[CH:19][C:18]=2[NH:24][C:25]([CH:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[O:26])=[N:13][CH:14]=1.[C:34](O)(=O)C.C([BH3-])#N.[Na+].C([O-])(=O)C.[NH4+]>CO.CC(C)=O>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:16](=[O:33])[C:17]2[CH:22]=[C:21]([I:23])[CH:20]=[CH:19][C:18]=2[NH:24][C:25]([CH:27]2[CH2:28][CH2:29][N:30]([CH:2]([CH3:3])[CH3:34])[CH2:31][CH2:32]2)=[O:26])=[N:13][CH:14]=1

参加物

7

反応物 4

HCID 176Acetic AcidHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 21906457N-(5-chloropyridin-2-yl)-5-iodo-2-[(4-piperidinylcarbonyl)amino]benzamide trifluoroacetate

生成物 1

HCID 21906277N-(5-chloropyridin-2-yl)-5-iodo-2-[(1-isopropylpiperidin-4-ylcarbonyl)amino]benzamide収率 65.5%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 887Methanol溶媒

実験手順

To a stirring suspension of N-(5-chloropyridin-2-yl)-5-iodo-2-[(4-piperidinylcarbonyl)amino]benzamide trifluoroacetate (1.5 g, 2.52 mmol) in methanol (25 mL) was added acetone (25 mL), followed by acetic acid (0.6 mL, 10 mmol), and then sodium cyanoborohydride (0.67 g, 10 mmol). After stirring overnight, the solution was treated with saturated aqueous ammonium acetate solution, concentrated, and partitioned between dichloromethane and saturated aqueous sodium bicarbonate. The organic phase was washed with brine, dried over magnesium sulfate, filtered, and concentrated. The crude product was purified by chromatography over silica gel, eluting with a step gradient of 5–15% 2 M solution of ammonia/methanol in dichloromethane. The chromatography product was slurried in diethyl ether and filtered to give 0.87 g (65%) of a white solid.

後処理

  1. concentrationconcentrated
  2. custompartitioned between dichloromethane and saturated aqueous sodium bicarbonate
  3. washThe organic phase was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by chromatography over silica gel
  8. washeluting with a step gradient of 5–15% 2 M solution of ammonia/methanol in dichloromethane
  9. filtrationfiltered

出典と根拠

ORDレコード
ord-27e8004c40f7499d8a9094ba59ca6168
出典データセット
uspto-grants-2006_10
特許番号
US07129245B2

反応ノート

読み込み中…