Oxalyl chloride → HCID 22379888, compound

HRID 895528Notes

Reaction equation

HRID 895528 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=O.[CH2:7]([N:9]1[C:13]2[CH:14]=[CH:15]C(C([O-])=O)=[CH:17][C:12]=2[N:11]=[C:10]1[CH2:21][C:22]1[N:23]([C:27]2[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:28]=2[F:34])[N:24]=[CH:25][CH:26]=1)[CH3:8]>CN(C=O)C.ClCCl>[CH2:10]([NH:9][C:1]([C:2]1[CH:15]=[CH:14][C:13]2[N:9]([CH2:7][CH3:8])[C:10]([CH2:21][C:22]3[N:23]([C:27]4[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:28]=4[F:34])[N:24]=[CH:25][CH:26]=3)=[N:11][C:12]=2[CH:17]=1)=[O:5])[C:21]#[CH:22]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 22380359HCID 22380359, compound

Product 1

HCID 22379888HCID 22379888, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Oxalyl chloride (2.5 eq of 2M in dichloromethane) is added dropwise to a solution of 1-ethyl-2-{[2-(2,5-difluorophenyl)-pyrazol-3-yl]methyl}-1H-benzimidazole-5-carboxylate (368 mg) in DMF (5 drops) and dichlormethane (30 mL) at 0° C. The mixture is stirred at 0° C. for 0.5 h, then at room temperature for 1 h. The solution is concentrated, the residue taken up in DMF (30 ml), excess propargylamine added, and the mixture stirred for 6 h. Dilute aqueous sodium bicarbonate is added then extracted with dichloromethane (3×), the combined organic layers washed with saturated aqueous sodium chloride, dried (MgSO4), and concentrated to give 462 mg of crude N-propargyl 1-ethyl-2-{[2-(2,5-difluorophenyl)-pyrazol-3-yl]methyl}-1H-benzimidazole-5-carboxamide.

Workup

  1. waitat room temperature for 1 h
  2. concentrationThe solution is concentrated
  3. additionexcess propargylamine added
  4. stirringthe mixture stirred for 6 h
  5. additionDilute aqueous sodium bicarbonate is added
  6. extractionthen extracted with dichloromethane (3×)
  7. washthe combined organic layers washed with saturated aqueous sodium chloride
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-8788de4f97ad46c599c38697587219e9
Source dataset
uspto-grants-2005_07
Patent number
US06916819B2

Reaction notes

Loading…