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

HRID 12135

반응식

HRID 12135 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 24288Cobalt(II) chloride촉매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-25ac70975bee4da599786cc6820b43b6
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727982B2

연결된 노트

불러오는 중…