Lithium borohydride → HCID 68771245, compound

HRID 1628437Notes

Reaction equation

HRID 1628437 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([NH:11][C:12]3[C:17]([CH3:18])=[CH:16][C:15]([Cl:19])=[CH:14][C:13]=3[O:20][CH3:21])[N:7]([CH:22]([CH2:28][CH3:29])[C:23](OCC)=[O:24])[C:6]=2[C:5]([CH:30]([CH2:33][CH3:34])[CH2:31][CH3:32])=[CH:4][CH:3]=1.[BH4-].[Li+]>O1CCCC1.O>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([NH:11][C:12]3[C:17]([CH3:18])=[CH:16][C:15]([Cl:19])=[CH:14][C:13]=3[O:20][CH3:21])[N:7]([CH:22]([CH2:28][CH3:29])[CH2:23][OH:24])[C:6]=2[C:5]([CH:30]([CH2:31][CH3:32])[CH2:33][CH3:34])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 4148881Lithium borohydride2×HCID 86632865HCID 86632865, compound

Product 1

HCID 68771245HCID 68771245, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl {4-chloro-2-[(4-chloro-2-methoxy-6-methylphenyl)amino]-7-(1-ethylpropyl)-1H-benzimidazol-1-yl}butanoate (100 mg, 0.197 mmol) in tetrahydrofuran (1.5 mL) was added lithium tetrahydroborate (13 mg, 0.597 mmol), and the mixture was stirred at room temperature for 84 hr. An additional lithium tetrahydroborate (26 mg, 1.19 mmol) was added, followed by stirring at 50° C. for 24 hr. The mixture was diluted with water and extracted with ethyl acetate. The extracts were washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 20-50% ethyl acetate/n-hexane gradient mixture to give the title compound (61 mg, 0.132 mmol, 20%) as a colorless solid.

Workup

  1. stirringby stirring at 50° C. for 24 hr
  2. extractionextracted with ethyl acetate
  3. washThe extracts were washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with a 20-50% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-bf7e3542d02b4e13b0fd15b76359973e
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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