2-Aminopyridine → HCID 66976250, compound

HRID 1022766Notes

Reaction equation

HRID 1022766 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[O:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10][C@H:9]2[CH:22]=O)=[CH:4][C:3]=1[F:24].[N:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[NH2:31]>C1COCC1.CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[O:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:20])([CH3:21])[CH3:19])=[O:16])[CH2:10][C@H:9]2[CH2:22][NH:31][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][N:25]=2)=[CH:4][C:3]=1[F:24]

Participants

5

Reactant 2

HCID 104392-AminopyridineHCID 86663874HCID 86663874, compound

Product 1

HCID 66976250HCID 66976250, compoundYield 61.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl (6R,7R)-7-(4-chloro-3-fluorophenyl)-6-formyl-1,4-oxazepane-4-carboxylate (150 mg) and pyridin-2-amine (79 mg) in THF (1.3 mL) and methanol (0.1 ml) was added borane-2-picoline complex (90 mg), and the mixture was stirred at room temperature for 3 hr. The reaction mixture was concentrated under reduced pressure, the residue was stirred in 1 M aqueous hydrochloric acid solution, and neutralized with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with distilled water and brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (112 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. stirringthe residue was stirred in 1 M aqueous hydrochloric acid solution
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with distilled water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-00f46119faf54f46bdf5114b59be2698
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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