Dimethylformamide → HCID 24750598, compound

HRID 643698Notes

Reaction equation

HRID 643698 reaction equation
[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([S:14]([C:17]4([C:23](O)=[O:24])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)(=[O:16])=[O:15])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:3][CH2:2]1.S(Cl)(Cl)=O.C[N:36](C)C=O>>[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([S:14]([C:17]4([C:23]([NH2:36])=[O:24])[CH2:18][CH2:19][O:20][CH2:21][CH2:22]4)(=[O:16])=[O:15])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:26][C:27]([CH3:28])([CH3:29])[CH3:30])[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 68615736HCID 68615736, compound

Product 1

HCID 24750598HCID 24750598, compoundYield 92%

Procedure

A mixture of 4-{[1-(cyclopropylmethyl)-2-(2,2-dimethylpropyl)-1H-benzimidazol-5-yl]sulfonyl}tetrahydro-2H-pyran-4-carboxylic acid (Step B, 288 mg, 0.66 mmol), thionyl chloride and N,N-dimethylformamide (few drops) was stirred under reflux for 3 h. After concentration, the residue was dissolved in dichloromethane (10 mL) and aqueous ammonia (1 mL) was added. The mixture was stirred at room temperature for 4 days. Water was added and the organic layer was separated. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by pTLC (hexane:ethyl acetate=1:10 as eluent) to give the title compound (264 mg, 92%) as a white solid.

Workup

  1. temperatureunder reflux for 3 h
  2. concentrationAfter concentration
  3. dissolutionthe residue was dissolved in dichloromethane (10 mL)
  4. additionaqueous ammonia (1 mL) was added
  5. stirringThe mixture was stirred at room temperature for 4 days
  6. additionWater was added
  7. customthe organic layer was separated
  8. dry with materialThe organic layer was dried over sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by pTLC (hexane:ethyl acetate=1:10 as eluent)

Sources & evidence

ORD record
ord-22aa1dbfa17a4af7806f193b04459535
Source dataset
uspto-grants-2010_04
Patent number
US07700618B2

Reaction notes

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