Ethyl Acetate → HCID 58966571, compound

HRID 390750Notes

Reaction equation

HRID 390750 reaction equation
[CH3:1][CH:2](C)[CH:3]([C:10]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:11]=1[CH:12]=O)[N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.[NH2:23][C:24]1[CH:29]=[N:28][C:27]([Br:30])=[CH:26][N:25]=1.[BH4-].[Na+].C(OCC)(=O)C>C1COCC1.CO.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].O>[Br:30][C:27]1[N:28]=[CH:29][C:24]([NH:23][CH2:12][C:11]2[CH:14]=[C:15]([C:18]([F:21])([F:20])[F:19])[CH:16]=[CH:17][C:10]=2[CH:3]([N:4]2[CH2:5][CH2:6][O:7][CH2:8][CH2:9]2)[CH2:2][CH3:1])=[N:25][CH:26]=1

Participants

9

Reactant 4

HCID 8857Ethyl AcetateHCID 5995392-Amino-5-bromopyrazineHCID 4311764Sodium borohydrideHCID 86614960HCID 86614960, compound

Product 1

HCID 58966571HCID 58966571, compoundYield 49%

Reagents, catalysts & solvents 4

HCID 11026Titanium isopropoxideCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2-(2-Methyl-1-morpholin-4-yl-propyl)-5-trifluoromethyl-benzaldehyde (126 mg, 0.418 mmol) in THF (0.5 mL) was added 2-amino-5-bromopyrazine (81 mg, 0.465 mmol) followed by titanium isopropoxide (0.2 uL; 0.675 mmol). The resulting mixture was stirred at 70° C. for 16 hours. The reaction mixture was cooled to room temperature and diluted with MeOH (0.5 mL). To this was added sodium borohydride (20 mg, 0.528 mmol). The resulting mixture is stirred at room temperature for 16 hours. Ethyl acetate and water were added and stirred for 15 minutes. Reaction is poured over a pad of celite and silica gel. The mother liquor is washed with water (2×) and brine. The organic layer is dried with anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (silica gel) (eluting with 10-50% ethyl acetate/hexanes) to afford the title compound (97 mg, 0.205 mmol).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringThe resulting mixture is stirred at room temperature for 16 hours
  3. stirringstirred for 15 minutes
  4. customReaction
  5. additionis poured over a pad of celite and silica gel
  6. washThe mother liquor is washed with water (2×) and brine
  7. dry with materialThe organic layer is dried with anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by flash chromatography (silica gel) (eluting with 10-50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-62a85f7175b24a97972bdb78cbf255dc
Source dataset
uspto-grants-2013_02
Patent number
US08383660B2

Reaction notes

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