HCID 178477641, compound → HCID 178477637, compound

HRID 1671649Notes

Reaction equation

HRID 1671649 reaction equation
[CH2:1]([S:3]([C:6]1[CH:33]=[CH:32][C:9]([O:10][C:11]2[C:12]([CH:26]([OH:31])[CH2:27][CH2:28][CH2:29]O)=[CH:13][C:14]3[N:18]=[C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=4)[NH:16][C:15]=3[CH:25]=2)=[CH:8][CH:7]=1)(=[O:5])=[O:4])[CH3:2]>C(Cl)(Cl)Cl>[O:31]1[CH2:29][CH2:28][CH2:27][CH:26]1[C:12]1[C:11]([O:10][C:9]2[CH:32]=[CH:33][C:6]([S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])=[CH:7][CH:8]=2)=[CH:25][C:15]2[NH:16][C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)=[N:18][C:14]=2[CH:13]=1

Participants

3

Reactant 1

HCID 178477641HCID 178477641, compound

Product 1

HCID 178477637HCID 178477637, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

P-toluenesulfonic acid monohydrate (20 mg) was added to a chloroform (4 ml) solution of 1-(6-(4-(ethylsulfonyl)phenoxy)-2-pyridin-2-yl-1H-benzimidazol-5-yl)butane-1,4-diol (81 mg) obtained in (step 1), and the reaction liquid was stirred overnight with heating under reflux. The solvent was evaporated away under reduced pressure, and the reaction mixture was purified through reversed-phase middle-pressure liquid chromatography (ODS-AS-360-CC (by YMC), mobile phase: water/acetonitrile/0.1% trifluoroacetic acid), and the resulting fraction was diluted with ethyl acetate, washed with aqueous saturated sodium bicarbonate and saturated saline water in that order, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure to obtain the entitled compound as a white solid.

Workup

  1. customobtained in (step 1)
  2. customthe reaction liquid
  3. temperaturewith heating
  4. temperatureunder reflux
  5. customThe solvent was evaporated away under reduced pressure
  6. customthe reaction mixture was purified through reversed-phase middle-pressure liquid chromatography (ODS-AS-360-CC (by YMC), mobile phase: water/acetonitrile/0.1% trifluoroacetic acid)
  7. additionthe resulting fraction was diluted with ethyl acetate
  8. washwashed with aqueous saturated sodium bicarbonate and saturated saline water in that order
  9. dry with materialdried with anhydrous sodium sulfate
  10. customThe solvent was evaporated away under reduced pressure

Sources & evidence

ORD record
ord-5e033d5453d3454c83ae6a87d8b736ad
Source dataset
uspto-grants-2011_08
Patent number
US07994331B2

Reaction notes

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