HCID 117601614, compound → HCID 117601434, compound

HRID 1773679Notes

Reaction equation

HRID 1773679 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]([C:26](=[O:31])N(OC)C)[C:10]3[N:14]=[C:13]([O:15][CH2:16][CH3:17])[N:12]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:11]=3[CH:25]=2)=[C:5]([CH3:32])[O:4][N:3]=1.[C:33]1([Mg]Cl)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C1COCC1>[C:26]([C:9]1[C:10]2[N:14]=[C:13]([O:15][CH2:16][CH3:17])[N:12]([C:18]([O:20][C:21]([CH3:24])([CH3:22])[CH3:23])=[O:19])[C:11]=2[CH:25]=[C:7]([C:6]2[C:2]([CH3:1])=[N:3][O:4][C:5]=2[CH3:32])[CH:8]=1)(=[O:31])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

4

Reactant 2

HCID 117601614HCID 117601614, compoundHCID 178478979HCID 178478979, compound

Product 1

HCID 117601434HCID 117601434, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tert-butyl 6-(3,5-dimethylisoxazol-4-yl)-2-ethoxy-4-(methoxy(methyl)carbamoyl)-1H-benzo[d]imidazole-1-carboxylate was dissolved in THF (3 mL). To the solution was added a solution of phenyl magnesium chloride (2M in THF, 0.508 mmol, 0.254 mmol) at −78° C. after the addition, the reaction was allowed to warm up to room temperature. The reaction was stirred for 17 hat the same temperature. The reaction mixture was quenched with water (30 mL). The whole was extracted with AcOEt (30 mL×3). Organic layer was washed with brine (30 mL) and dried over Na2SO4. The solvent was removed under a reduced pressure to give the crude product. The crude product was purified by a silica gel column chromatography (hexane:EtOAc, 7:1 to 3:1) to give tert-butyl 4-benzoyl-6-(3,5-dimethylisoxazol-4-yl)-2-ethoxy-1H-benzo[d]imidazole-1-carboxylate.

Workup

  1. additionafter the addition
  2. customThe reaction mixture was quenched with water (30 mL)
  3. extractionThe whole was extracted with AcOEt (30 mL×3)
  4. washOrganic layer was washed with brine (30 mL)
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed under a reduced pressure
  7. customto give the crude product
  8. customThe crude product was purified by a silica gel column chromatography (hexane:EtOAc, 7:1 to 3:1)

Sources & evidence

ORD record
ord-f7049a52f6614508a13b1bbec18c446b
Source dataset
uspto-grants-2016_02
Patent number
US09255089B2

Reaction notes

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