Sodium Methoxide → HCID 135839369, compound

HRID 2221045Notes

Reaction equation

HRID 2221045 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][C:11]([NH:13][C:14]1[NH:18][N:17]=[CH:16][C:15]=1[C:19]#[N:20])=[O:12].C[O-].[Na+]>O>[NH2:20][C:19]1[C:15]2[CH:16]=[N:17][NH:18][C:14]=2[NH:13][C:11](=[O:12])[C:10]=1[C:2]1[NH:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 21883425HCID 21883425, compound

Product 1

HCID 135839369HCID 135839369, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(1H-Benzimidazol-2-yl)—N-(4-cyano-1H-pyrazol-5-yl)acetamide (1.0 eq) was heated in NaOMe (20 eq, 0.5 M in MeOH) at 100° C. for 2 days. H2O was added, and the mixture was extracted with EtOAc. The organic layer was washed with H2O and brine, dried over Na2SO4, filtered, and concentrated in vacuo to yield a solid. The material was purified by reverse phase HPLC. LC/MS m/z 267.1 (MH+), Rt 1.57 minutes.

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. washThe organic layer was washed with H2O and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto yield a solid
  7. customThe material was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-88fdcfb6704d483ca232f04909293d15
Source dataset
uspto-grants-2008_05
Patent number
US07368459B2

Reaction notes

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