Sulfuric Acid → HCID 178477642, compound

HRID 1671654Notes

Reaction equation

HRID 1671654 reaction equation
S(=O)(=O)(O)[OH:2].[CH2:6]([S:8]([C:11]1[CH:40]=[CH:39][C:14]([O:15][C:16]2[C:17]([CH:31]([O:34][Si](C)(C)C)[C:32]#[N:33])=[CH:18][C:19]3[N:23]=[C:22]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=4)[NH:21][C:20]=3[CH:30]=2)=[CH:13][CH:12]=1)(=[O:10])=[O:9])[CH3:7]>>[CH2:6]([S:8]([C:11]1[CH:40]=[CH:39][C:14]([O:15][C:16]2[C:17]([CH:31]([OH:34])[C:32]([NH2:33])=[O:2])=[CH:18][C:19]3[N:23]=[C:22]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=4)[NH:21][C:20]=3[CH:30]=2)=[CH:13][CH:12]=1)(=[O:10])=[O:9])[CH3:7]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 178477640HCID 178477640, compound

Product 1

HCID 178477642HCID 178477642, compound

Procedure

80% sulfuric acid (0.2 ml) was added to (6-(4-(ethylsulfonyl)phenoxy)-2-pyridin-2-yl-1H-benzimidazol-5-yl)((trimethylsilyl(oxy)acetonitrile (25 mg) obtained in Example 31 (step 1), and the reaction liquid was stirred at room temperature for 3 hours. 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.

Workup

  1. customthe reaction liquid
  2. 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)
  3. additionthe resulting fraction was diluted with ethyl acetate
  4. washwashed with aqueous saturated sodium bicarbonate and saturated saline water in that order
  5. dry with materialdried with anhydrous sodium sulfate
  6. customThe solvent was evaporated away under reduced pressure
  7. customto obtain the entitled compound

Sources & evidence

ORD record
ord-51a2d45f84194c1d8371b5e567882f35
Source dataset
uspto-grants-2011_08
Patent number
US07994331B2

Reaction notes

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