2-Aminopyridine → HCID 22731092, compound

HRID 2085373Notes

Reaction equation

HRID 2085373 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[H-].[Na+].Br[C:11]1[S:12][C:13](/[CH:16]=[CH:17]/[C:18]2[O:19][C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:21][N:22]=2)=[CH:14][N:15]=1>C1COCC1>[C:23]([C:20]1[O:19][C:18](/[CH:17]=[CH:16]/[C:13]2[S:12][C:11]([N:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]3[NH2:1])=[N:15][CH:14]=2)=[N:22][CH:21]=1)([CH3:26])([CH3:24])[CH3:25]

Participants

5

Reactant 3

HCID 104392-AminopyridineHCID 24758Sodium hydrideHCID 22731087HCID 22731087, compound

Product 1

HCID 22731092HCID 22731092, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-aminopyridine (238 mg, 2.56 mmol) in THF (8 mL) under argon was added sodium hydride (100 mg of 60% oil dispersion, 2.5 mmol) and the reaction stirred at 60 deg C. for 15 minutes, cooled to room temperature and 2-bromo-[(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazole] (200 mg, 0.64 mmol) was added in one portion. The reaction mixture was stirred for 20 minutes, quenched with hydrochloric acid, washed with water and extracted with ethyl acetate. The organic layers were separated and concentrated to give a crude product which was heated with ethyl acetate: hexanes (1:1), cooled, filtered, and dried under vacuum to give the desired product. C17H18N4OS, MS m/e 327 (M+H)+. HPLC-HI 100% at 4.24 min (YMC S5 ODS column 4.6×50 mm, 10-90% aqueous methanol over 4 minutes containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm).

Workup

  1. stirringThe reaction mixture was stirred for 20 minutes
  2. customquenched with hydrochloric acid
  3. washwashed with water
  4. extractionextracted with ethyl acetate
  5. customThe organic layers were separated
  6. concentrationconcentrated
  7. customto give a crude product which
  8. temperaturecooled
  9. filtrationfiltered
  10. customdried under vacuum

Sources & evidence

ORD record
ord-06b6e042f5114ed8af3b5978aff15675
Source dataset
uspto-grants-2004_04
Patent number
US06720347B2

Reaction notes

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