Lithium borohydride → HCID 68763066, compound

HRID 1628435Notes

Reaction equation

HRID 1628435 reaction equation
[BH4-].[Li+].[Cl:3][C:4]1[C:12]2[N:11]=[C:10]([NH:13][C:14]3[C:15]([O:20][CH3:21])=[N:16][CH:17]=[CH:18][CH:19]=3)[N:9]([CH2:22][CH2:23][CH2:24][C:25](OCC)=[O:26])[C:8]=2[C:7]([CH:30]([CH2:33][CH3:34])[CH2:31][CH3:32])=[CH:6][CH:5]=1>O1CCCC1>[Cl:3][C:4]1[C:12]2[N:11]=[C:10]([NH:13][C:14]3[C:15]([O:20][CH3:21])=[N:16][CH:17]=[CH:18][CH:19]=3)[N:9]([CH2:22][CH2:23][CH2:24][CH2:25][OH:26])[C:8]=2[C:7]([CH:30]([CH2:33][CH3:34])[CH2:31][CH3:32])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 68765025HCID 68765025, compound

Product 1

HCID 68763066HCID 68763066, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of lithium borohydride (45.6 mg, 2.09 mmol) in tetrahydrofuran (5 mL) was added ethyl 4-{4-chloro-7-(1-ethylpropyl)-2-[(2-methoxypyridin-3-yl)amino]-1H-benzimidazol-1-yl}butanoate (320 mg, 0.697 mmol) at 0° C. The mixture was stirred at room temperature for 6 hr. The reaction mixture was quenched with water and extracted with ethyl acetate (×3). The organics were dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 10-50% ethyl acetate/n-hexane gradient mixture to give the title compound (250 mg, 0.60 mmol, 86%) as a white amorphous.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with ethyl acetate (×3)
  3. dry with materialThe organics were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with 10-50% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-3c4907f3e9644037b18ca70088daa169
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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