Sodium sulfate decahydrate → 4-[2-[(2,4-Dichlorophenyl)amino]-7-(diethylamino)-1H-benzimidazol-1-yl]butane-1,3-diol

HRID 1398806Notes

Reaction equation

HRID 1398806 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[NH:15][C:16]1[N:20]([CH2:21][CH:22]([OH:28])[CH2:23][C:24](OC)=[O:25])[C:19]2[C:29]([N:33]([CH2:36][CH3:37])[CH2:34][CH3:35])=[CH:30][CH:31]=[CH:32][C:18]=2[N:17]=1.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[Cl:7][C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[NH:15][C:16]1[N:20]([CH2:21][CH:22]([OH:28])[CH2:23][CH2:24][OH:25])[C:19]2[C:29]([N:33]([CH2:36][CH3:37])[CH2:34][CH3:35])=[CH:30][CH:31]=[CH:32][C:18]=2[N:17]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 68765145Methyl 4-[2-[(2,4-dichlorophenyl)amino]-7-(diethylamino)-1H-benzimidazol-1-yl]-3-hydroxybutanoate

Product 1

HCID 687631674-[2-[(2,4-Dichlorophenyl)amino]-7-(diethylamino)-1H-benzimidazol-1-yl]butane-1,3-diolYield 96.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (15.9 mg, 0.429 mmol) in tetrahydrofuran (1 mL) was added a solution of methyl 4-[2-[(2,4-dichlorophenyl)amino]-7-(diethylamino)-1H-benzimidazol-1-yl]-3-hydroxybutanoate (Reference Example 83; 50.0 mg, 0.107 mmol) in tetrahydrofuran (1 mL) at 0° C. and the resultant mixture was stirred at 0° C. for 10 min. After sodium sulfate decahydrate (500 mg) was added at 0° C., the resultant mixture was filtered and concentrated in vacuo to give the title compound as an oil (45.0 mg, 0.103 mmol, 96%).

Workup

  1. filtrationthe resultant mixture was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8f216302d8b14299b60392f1bf69f224
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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