HCID 20814073, compound → HCID 69719549, compound

HRID 896380Notes

Reaction equation

HRID 896380 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][F:22])=[C:7]([NH:9][C:10]([CH2:12][O:13][C:14](=[O:16])[CH3:15])=O)[CH:8]=1)#[N:2]>CC(O)=O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[N:17]([CH2:18][CH2:19][CH2:20][CH2:21][F:22])[C:10]([CH2:12][O:13][C:14](=[O:16])[CH3:15])=[N:9][C:7]=2[CH:8]=1)#[N:2]

Participants

3

Reactant 1

HCID 20814073HCID 20814073, compound

Product 1

HCID 69719549HCID 69719549, compoundYield 55.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Acetic acid [5-cyano-2-(4-fluoro-butylamino)-phenylcarbamoyl]-methyl ester (2.5 g, 8.14 mmol)was dissolved in AcOH (20 mL) and heated to reflux for 2 h. The reaction mixture was concentrated and the residue dissolved in EtOAc and washed with saturated NaHCO3. The organic layer is dried over MgSO4 and concentrated to give 1.3 g (55%) of acetic acid 5-cyano-1-(4-fluoro-butyl)-1H-benzoimidazol-2-ylmethyl ester as a dark solid.

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 h
  3. concentrationThe reaction mixture was concentrated
  4. dissolutionthe residue dissolved in EtOAc
  5. washwashed with saturated NaHCO3
  6. dry with materialThe organic layer is dried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-493ca3e546a24b35995744560f70ef0b
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

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