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

HRID 12164
Notes
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Reaction equation

HRID 12164 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 24288Cobalt(II) chlorideCatalyst
HCID 6228
Dimethylformamide
Solvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a33abca967ae4d04826e526108b5ff3e
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07727981B2

Reaction notes

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