Aluminium lithium hydride → HCID 178477643, compound

HRID 1671656Notes

Reaction equation

HRID 1671656 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])[C:27](OC)=[O:28])=[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].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[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][OH:28])=[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:4])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178477645HCID 178477645, compound

Product 1

HCID 178477643HCID 178477643, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a tetrahydrofuran (1.5 ml) solution of methyl (6-(4-(ethylsulfonyl)phenoxy)-2-pyridin-2-yl-1H-benzimidazol-5-yl)(hydroxy)acetate (30 mg) obtained in Example 31 (step 2), added was lithiumaluminium hydride (10 mg), and the reaction liquid was stirred at 0° C. for 10 minutes. Sodium sulfate 10-hydrate was added to the reaction liquid, and stirred overnight at room temperature. Then, the residue was removed through filtration through Celite, and the solvent was evaporated away under reduced pressure. The resulting residue 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. stirringstirred overnight at room temperature
  3. customThen, the residue was removed through filtration through Celite
  4. customthe solvent was evaporated away under reduced pressure
  5. customThe resulting residue was purified through reversed-phase middle-pressure liquid chromatography (ODS-AS-360-CC (by YMC), mobile phase: water/acetonitrile/0.1% trifluoroacetic acid)
  6. additionthe resulting fraction was diluted with ethyl acetate
  7. washwashed with aqueous saturated sodium bicarbonate and saturated saline water in that order
  8. dry with materialdried with anhydrous sodium sulfate
  9. customThe solvent was evaporated away under reduced pressure
  10. customto obtain the entitled compound

Sources & evidence

ORD record
ord-6cb59ed027aa4cf9bcc3bd1094add19e
Source dataset
uspto-grants-2011_08
Patent number
US07994331B2

Reaction notes

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