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

HRID 12163
Notes
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Reaction equation

HRID 12163 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]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]#[N:33])=[CH:22][CH:21]=2)=[O:19])=[O:10])=[N:6][CH:7]=1.[BH4-].[Na+]>CN(C=O)C.[Co](Cl)Cl>[NH2:33][CH2:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[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 22596431N-{2-[N-(5-chloro(2-pyridyl))carbamoyl]phenyl}[4-(2-cyanophenyl)phenyl)carboxamide

Product 1

HCID 18727717{4-[2-(Aminomethyl)phenyl]phenyl}-n-{2-[n-(5-chloro(2-pyridyl))carbamoyl]-phenyl}carboxamideYield 43.1%

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-(2-cyanophenyl)phenyl]carboxamide (200 mg, 0.442 mmol, 1.0 equiv.), cobalt chloride (86 mg, 0.664 mmol, 1.5 equiv.) and sodium borohydride (50 mg, 1.33 mmol, 3.0 equiv.) in DMF (15 mL) was stirred at 0° C. to rt for 3 days. The reaction was quenched with ice cubes, diluted with DCM (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-[2-(aminomethyl)phenyl]phenyl}-N-{2-[N-(5-chloro(2-pyridyl))carbamoyl]phenyl}carboxamide (87 mg, 43%). MS found for C26H21ClN4O2 (M+H)+: 457.

Workup

  1. customThe reaction was quenched with ice cubes
  2. additiondiluted with DCM (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-e07f07c233194fffb8fe4e88631f016a
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07727981B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes