Sodium borohydride → [4-(Aminomethyl)phenyl]-n-{2-[n-(5-chloro(2-pyridyl))carbamoyl]phenyl}carboxamide

HRID 12164

反応式

HRID 12164 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[NH:17][C:18]([C:20]2[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][CH:21]=2)=[O:19])=[O:10])=[N:6][CH:7]=1.[BH4-].[Na+]>CN(C=O)C.[Co](Cl)Cl>[NH2:27][CH2:26][C:23]1[CH:22]=[CH:21][C:20]([C:18]([NH:17][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[C:9](=[O:10])[NH:8][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=2)=[O:19])=[CH:25][CH:24]=1

参加物

5

反応物 2

HCID 4311764Sodium borohydrideHCID 22596336n-{2-[n-(5-Chloro(2-pyridyl))carbamoyl]phenyl}(4-cyanophenyl)carboxamide

生成物 1

HCID 18727608[4-(Aminomethyl)phenyl]-n-{2-[n-(5-chloro(2-pyridyl))carbamoyl]phenyl}carboxamide収率 32.3%

試薬・触媒・溶媒 2

HCID 24288Cobalt(II) chloride触媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of N-{2-[N-(5-chloro(2-pyridyl))carbamoyl]phenyl}(4-cyanophenyl)carboxamide (1 g, 2.6 mmol, 1.0 equiv.), cobalt chloride (0.5 g, 3.85 mmol, 1.5 equiv.) and sodium borohydride (0.295 g, 7.8 mmol, 3.0 equiv.) in DMF (20 mL) was stirred at 0° C. to rt for 2.5 hr. The reaction was quenched with ice cubes, diluted with ethyl acetate (100 mL) and filtered through celite. The filtrate was washed with saturated aqueous NaHCO3. The organic layer was dried over MgSO4, filtered, evaporated and HPLC (C18 reversed phase) eluting with 0.1% TFA in H2O/CH3CN gave [4-(aminomethyl)phenyl]-N-{2-[N-(5-chloro(2-pyridyl))carbamoyl]phenyl}carboxamide (320 mg, 30%). MS found for C20H17ClN4O2 (M+H)+: 381.

後処理

  1. customThe reaction was quenched with ice cubes
  2. additiondiluted with ethyl acetate (100 mL)
  3. filtrationfiltered through celite
  4. washThe filtrate was washed with saturated aqueous NaHCO3
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. washHPLC (C18 reversed phase) eluting with 0.1% TFA in H2O/CH3CN

出典と根拠

ORDレコード
ord-a33abca967ae4d04826e526108b5ff3e
出典データセット
uspto-grants-2010_06
特許番号
US07727981B2

関連ノート

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