Ethyl ketone → HCID 59594569, compound

HRID 2262689Notes

Reaction equation

HRID 2262689 reaction equation
[Cl:1][C:2]1[C:3]([CH3:10])=[C:4]([NH2:9])[C:5]([NH2:8])=[N:6][CH:7]=1.[CH3:11][CH2:12][C:13](=O)[CH2:14][CH3:15].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1.C(O)(C(F)(F)F)=O.CCOC(C)=O>[Cl:1][C:2]1[C:3]([CH3:10])=[C:4]([NH:9][CH:13]([CH2:14][CH3:15])[CH2:12][CH3:11])[C:5]([NH2:8])=[N:6][CH:7]=1

Participants

7

Reactant 3

HCID 7288Ethyl ketoneHCID 5049666Sodium triacetoxyborohydrideHCID 445580925-Chloro-4-methylpyridine-2,3-diamine

Product 1

HCID 59594569HCID 59594569, compoundYield 17.1%

Reagents, catalysts & solvents 3

HCID 6422Trifluoroacetic acidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a room-temperature solution of 5-chloro-4-methylpyridine-2,3-diamine (200 mg, 1.27 mmol, 1.0 equiv) and 3-pentanone (400 uL, 3.78 mmol, 3.0 equiv) in THF (0.5 mL) and TFA (0.5 mL) was added sodium triacetoxyborohydride (807 mg, 3.81 mmol, 3.0 equiv) as a solid in one portion. The resulting mixture was allowed to stir overnight at room temperature. The reaction was then diluted with EtOAc and washed with saturated aq. NaHCO3. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by reverse phase HPLC to provide the title compound (49.4 mg, 17%). m/z=228.1 [M+H]+

Workup

  1. washwashed with saturated aq. NaHCO3
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-4eae5a964c9c47009ac8398453d2c84a
Source dataset
uspto-grants-2010_12
Patent number
US07851484B2

Reaction notes

Loading…