4-(6-Amino-3-pyridinyl)benzonitrile → HCID 86699097, compound

HRID 1424206Notes

Reaction equation

HRID 1424206 reaction equation
Br[CH2:2][C:3](=O)[C@@H:4]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@@H:5]([CH3:16])[C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].[NH2:26][C:27]1[N:32]=[CH:31][C:30]([C:33]2[CH:40]=[CH:39][C:36]([C:37]#[N:38])=[CH:35][CH:34]=2)=[CH:29][CH:28]=1>C1COCC1.C([O-])(O)=O.[Na+]>[C:21]([O:20][C:18]([NH:17][C@H:4]([C:3]1[N:26]=[C:27]2[CH:28]=[CH:29][C:30]([C:33]3[CH:40]=[CH:39][C:36]([C:37]#[N:38])=[CH:35][CH:34]=3)=[CH:31][N:32]2[CH:2]=1)[C@@H:5]([CH3:16])[C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])=[O:19])([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 2

HCID 200998134-(6-Amino-3-pyridinyl)benzonitrileHCID 86699121HCID 86699121, compound

Product 1

HCID 86699097HCID 86699097, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of benzyl (2R,3S)-5-bromo-3-[(tert-butoxycarbonyl)amino]-2-methyl-4-oxopentanoate (Preparation 65, 400 mg, 0.966 mmol) in THF (15 mL) was added 4-(6-aminopyridin-3-yl)benzonitrile and the reaction stirred at room temperature for 3 days followed by 40° C. for 18 hours. The reaction was diluted with saturated aqueous NaHCO3 solution (80 mL), and extracted with EtOAc (3×50 mL). The organic layers were collected, dried over MgSO4 and concentrated in vacuo. The residue was purified by reverse phase column chromatography eluting with 0-60% MeCN in water followed by silica gel column chromatography eluting with 40% EtOAc in heptanes to afford the title compound.

Workup

  1. waitfollowed by 40° C. for 18 hours
  2. extractionextracted with EtOAc (3×50 mL)
  3. customThe organic layers were collected
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by reverse phase column chromatography
  7. washeluting with 0-60% MeCN in water
  8. washeluting with 40% EtOAc in heptanes

Sources & evidence

ORD record
ord-32effb8bc3a84002880c59e99769e591
Source dataset
uspto-grants-2015_01
Patent number
US08927587B2

Reaction notes

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