Water → HCID 71272254, compound

HRID 475087Notes

Reaction equation

HRID 475087 reaction equation
[CH3:1][CH2:2][Mg+].[Br-].CON(C)[C:8]([C:10]1[CH:24]=[CH:23][C:13]2[N:14]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][O:18]3)[CH:15]=[N:16][C:12]=2[CH:11]=1)=[O:9].[NH4+].[Cl-].O>C1COCC1>[O:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH:17]1[N:14]1[C:13]2[CH:23]=[CH:24][C:10]([C:8](=[O:9])[CH2:2][CH3:1])=[CH:11][C:12]=2[N:16]=[CH:15]1

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 86694687HCID 86694687, compoundHCID 178461630HCID 178461630, compound

Product 1

HCID 71272254HCID 71272254, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of EtMgBr (0.72 mL, 1 mol/L) was added to N-methoxy-N-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazole-5-carboxamide (70 mg, 0.24 mmol) in THF at 0° C. under argon. The mixture was stirred at 0° C. for 2 h. A solution of NH4Cl was added, carefully, to quench the reaction. The mixture was poured into water and extracted with EtOAc. The organics were washed sequentially with water and brine, then dried (Na2SO4). Removal of solvent followed by SiO2 chromatography afforded 1-(1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)propan-1-one as a colorless oil (45 mg, 72% yield).

Workup

  1. customcarefully, to quench
  2. customthe reaction
  3. extractionextracted with EtOAc
  4. washThe organics were washed sequentially with water and brine
  5. dry with materialdried (Na2SO4)
  6. customRemoval of solvent

Sources & evidence

ORD record
ord-33970f9dc0534989a06f64bb141167b7
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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