ethyl 2-(1H-1,3-benzodiazol-2-yl)acetate → HCID 136348951, compound

HRID 1883937Notes

Reaction equation

HRID 1883937 reaction equation
[Li]C(C)(C)C.[N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][C:7]=1[CH2:15][C:16]([O:18]CC)=O.[NH2:21][C:22]1[C:27]([C:28]#[N:29])=[C:26]([N:30]2[CH2:35][CH2:34][N:33]([CH2:36][CH3:37])[CH2:32][CH2:31]2)[CH:25]=[CH:24][CH:23]=1>C1COCC1>[NH2:29][C:28]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][C:26]=2[N:30]2[CH2:31][CH2:32][N:33]([CH2:36][CH3:37])[CH2:34][CH2:35]2)[NH:21][C:16](=[O:18])[C:15]=1[C:7]1[NH:6][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=1

Participants

5

Reactant 3

HCID 308071ethyl 2-(1H-1,3-benzodiazol-2-yl)acetateHCID 22664648HCID 22664648, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 136348951HCID 136348951, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

t-BuLi (3.1 eq) was added to ethyl 2-benzimidazol-2-ylacetate (1.0 eq) and 6-amino-2-(4-ethylpiperazinyl)benzenecarbonitrile (1.0 eq) in THF at 0° C. The reaction was stirred overnight. The resulting mixture was quenched with NH4Cl (aq, saturated) and extracted with EtOAc. The combined organic layers were washed with H2O and brine, dried over Na2SO4, filtered, and concentrated in vacuo to yield a brown solid. The crude material was triturated with CH2Cl2 and MeOH to provide a tan solid. LC/MS m/z 389.1 (MH+), Rt 1.80 minutes.

Workup

  1. customThe resulting mixture was quenched with NH4Cl (aq, saturated)
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with H2O and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto yield a brown solid
  8. customThe crude material was triturated with CH2Cl2 and MeOH
  9. customto provide a tan solid

Sources & evidence

ORD record
ord-479c504e130147c986972bedcd118de3
Source dataset
uspto-grants-2004_07
Patent number
US06762194B2

Reaction notes

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