Tetrahydrofuran → HCID 86716191, compound

HRID 512165Notes

Reaction equation

HRID 512165 reaction equation
[F:1][C:2]1([F:17])[CH2:7][CH2:6][C:5]([N:11]2[CH:15]=[C:14]([CH3:16])[N:13]=[CH:12]2)([C:8]([NH2:10])=O)[CH2:4][CH2:3]1.C1COCC1.[AlH4-].[Li+]>>[F:17][C:2]1([F:1])[CH2:3][CH2:4][C:5]([CH2:8][NH2:10])([N:11]2[CH:15]=[C:14]([CH3:16])[N:13]=[CH:12]2)[CH2:6][CH2:7]1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 28112Lithium aluminum hydrideHCID 86716189HCID 86716189, compound

Product 1

HCID 86716191HCID 86716191, compoundYield 49.2%

Procedure

Into a round bottom flask was added 4,4-Difluoro-1-(4-methyl-imidazol-1-yl)-cyclohexanecarboxylic acid amide (99 mg, 0.39 mmol) and THF (10 mL, 100 mmol) at room temperature, to the reaction mixture was added lithium tetrahydroaluminate (365 mg, 9.62 mmol). The reaction was refluxed for 6 hours, before being quenched with water (0.4 ml), 2M NaOH (0.4 ml) and water (0.8 ml). The reaction mixture was filtered and cone. The residue was purified by flash column chromatography on silica gel (eluding w a mixture of 5% Et3N/10% MeOH185% AcOEt) to give the title compound (44 mg, 47%). 1H NMR (CDCl3 500 MHz): δppm 7.55 (s, 1H), 6.71 (s, 1H), 2.70 (s, 2H), 2.4-1.7 (m, 8H), 2.21 (s, 3H).

Workup

  1. temperatureThe reaction was refluxed for 6 hours
  2. custombefore being quenched with water (0.4 ml), 2M NaOH (0.4 ml) and water (0.8 ml)
  3. filtrationThe reaction mixture was filtered
  4. customThe residue was purified by flash column chromatography on silica gel (
  5. additiona mixture of 5% Et3N/10% MeOH185% AcOEt)

Sources & evidence

ORD record
ord-c791ffb802c04d8992383c941b48599d
Source dataset
uspto-grants-2015_08
Patent number
US09102591B2

Reaction notes

Loading…