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

HRID 2057098Notes

Reaction equation

HRID 2057098 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-36059f9359804c03837190890ea41d13
Source dataset
uspto-grants-2008_02
Patent number
US07335774B2

Reaction notes

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