Dimethylformamide → HCID 57708174, compound

HRID 643697Notes

Reaction equation

HRID 643697 reaction equation
[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([S:14]([CH2:17][C:18](OC)=[O:19])(=[O:16])=[O:15])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:34][CH2:35]Br.C[N:38](C=O)C>>[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([S:14]([C:17]4([C:18]([NH2:38])=[O:19])[CH2:35][CH2:34]4)(=[O:16])=[O:15])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:22][C:23]([CH3:24])([CH3:25])[CH3:26])[CH2:3][CH2:2]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 59253204HCID 59253204, compound

Product 1

HCID 57708174HCID 57708174, compoundYield 80%

Procedure

To a solution of methyl {[1-(cyclopropylmethyl)-2-(2,2-dimethylpropyl)-1H-benzimidazol-5-yl]sulfonyl}acetate (Example 1, Step F, 620 mg, 1.64 mmol) in N,N′-dimethylformamide (6.0 mL) was added potassium carbonate (680 mg, 4.91 mmol) and 1,2-dibromoethane (170 μL, 1.97 mmol) at room temperature and stirred for 30 h. The mixture was quenched with water (40 mL) and extracted with ethyl acetate (50 mL×3). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:2 as eluent) to afford the title compound (533 mg, 80%) as a white amorphous.

Workup

  1. customThe mixture was quenched with water (40 mL)
  2. extractionextracted with ethyl acetate (50 mL×3)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:2 as eluent)

Sources & evidence

ORD record
ord-c3f96bf2ea8d40f581fd8c00d3363345
Source dataset
uspto-grants-2010_04
Patent number
US07700618B2

Reaction notes

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