Thionyl Chloride → HCID 89702206, compound

HRID 2202901Notes

Reaction equation

HRID 2202901 reaction equation
S(Cl)(Cl)=O.[F:5][C:6]1[CH:36]=[CH:35][C:9]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][N:15]([C:18]3[CH:19]=[CH:20][C:21]4[N:25]=[C:24]([C:26]([NH:28][CH2:29][CH2:30]O)=[O:27])[N:23]([CH3:32])[C:22]=4[CH:33]=3)[C:14](=[O:34])[CH:13]=2)=[CH:8][CH:7]=1>C1COCC1>[O:27]1[CH2:30][CH2:29][N:28]=[C:26]1[C:24]1[N:23]([CH3:32])[C:22]2[CH:33]=[C:18]([N:15]3[CH:16]=[CH:17][C:12]([O:11][CH2:10][C:9]4[CH:8]=[CH:7][C:6]([F:5])=[CH:36][CH:35]=4)=[CH:13][C:14]3=[O:34])[CH:19]=[CH:20][C:21]=2[N:25]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 89691037HCID 89691037, compound

Product 1

HCID 89702206HCID 89702206, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Thionyl chloride (0.078 ml) was added to a mixture of 6-(4-((4-fluorobenzyl)oxy)-2-oxopyridin-1(2H)-yl)-N-(2-hydroxyethyl)-1-methyl-1H-benzimidazole-2-carboxamide (50.0 mg) in THF (2 ml) at room temperature. The mixture was stirred at room temperature for 3 h, and at 50° C. under Ar atmosphere for 2 h. After evaporation of the solvent, THF (2 ml) was added to the residue. NaH (40% oil dispersion, 34.3 mg) was added to the mixture at 0° C. The mixture was stirred at room temperature for 1 h, and at 50° C. under Ar atmosphere for 2 h. After addition of water (0.5 ml), the mixture was stirred at room temperature over weekend. The mixture was quenched with brine and extracted with EtOAc/THF. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated in vacuo. The solid was washed with EtOAc to give the title compound (17.9 mg) as a white solid.

Workup

  1. waitat 50° C. under Ar atmosphere for 2 h
  2. customAfter evaporation of the solvent, THF (2 ml)
  3. additionwas added to the residue
  4. additionNaH (40% oil dispersion, 34.3 mg) was added to the mixture at 0° C
  5. stirringThe mixture was stirred at room temperature for 1 h
  6. waitat 50° C. under Ar atmosphere for 2 h
  7. additionAfter addition of water (0.5 ml)
  8. stirringthe mixture was stirred at room temperature over weekend
  9. customThe mixture was quenched with brine
  10. extractionextracted with EtOAc/THF
  11. customThe organic layer was separated
  12. washwashed with brine
  13. dry with materialdried over MgSO4
  14. concentrationconcentrated in vacuo
  15. washThe solid was washed with EtOAc

Sources & evidence

ORD record
ord-867b2373c8f3429ea357887b720719b2
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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