HCID 117601197, compound → HCID 117601899, compound

HRID 1773744Notes

Reaction equation

HRID 1773744 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]([C:17]([O:19]C)=O)[C:10]3[NH:14][C:13](=[O:15])[NH:12][C:11]=3[CH:16]=2)=[C:5]([CH3:21])[O:4][N:3]=1.[CH:22]1([Mg]Cl)[CH2:26][CH2:25][CH2:24][CH2:23]1>C1COCC1>[CH:22]1([C:17]([C:9]2[C:10]3[NH:14][C:13](=[O:15])[NH:12][C:11]=3[CH:16]=[C:7]([C:6]3[C:2]([CH3:1])=[N:3][O:4][C:5]=3[CH3:21])[CH:8]=2)=[O:19])[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 117601197HCID 117601197, compoundHCID 178478989HCID 178478989, compound

Product 1

HCID 117601899HCID 117601899, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture containing methyl 6-(3,5-dimethylisoxazol-4-yl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-4-carboxylate (60 mg, 0.21 mmol, 1 equiv.) and THF (3 mL) is added cyclopentyl magnesium chloride (0.88 mL, 1.46 mmol, 7 equiv.) at 0° C. for 5 min. After completion, the reaction was quenched and extracted with EtOAc and washed with water, saturated NH4Cl. After drying with MgSO4, it was filtered and concentrated to dryness. Purification was carried out by reverse phase HPLC.

Workup

  1. customAfter completion, the reaction was quenched
  2. extractionextracted with EtOAc
  3. washwashed with water, saturated NH4Cl
  4. dry with materialAfter drying with MgSO4, it
  5. filtrationwas filtered
  6. concentrationconcentrated to dryness
  7. customPurification

Sources & evidence

ORD record
ord-154bd48e69d64f63bb8e9af71b0db646
Source dataset
uspto-grants-2016_02
Patent number
US09255089B2

Reaction notes

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