Lithium borohydride → HCID 68776774, compound

HRID 1628619Notes

Reaction equation

HRID 1628619 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=3[Cl:19])[N:7]([CH2:20][CH2:21][CH2:22][C:23](OCC)=[O:24])[C:6]=2[C:5]([CH:28]([CH2:31][CH3:32])[CH2:29][CH3:30])=[CH:4][CH:3]=1.[BH4-].[Li+]>O1CCCC1>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=3[Cl:19])[N:7]([CH2:20][CH2:21][CH2:22][CH2:23][OH:24])[C:6]=2[C:5]([CH:28]([CH2:31][CH3:32])[CH2:29][CH3:30])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 68737042HCID 68737042, compound

Product 1

HCID 68776774HCID 68776774, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-{4-chloro-2-[(2,4-dichlorophenyl)amino]-7-(1-ethylpropyl)-1H-benzimidazol-1-yl}butanoate (Reference Example 34; 453 mg, 0.920 mmol) in tetrahydrofuran (5 mL) was added lithium borohydride (60 mg, 2.76 mmol), and the mixture was refluxed for 2 hr. After cooled to room temperature, the reaction mixture was quenched with methanol (0.5 mL) and concentrated to dryness. The residue was partitioned between ethyl acetate (10 mL) and water (5 mL). The aqueous layer was extracted with ethyl acetate (10 mL×3), washed with brine (15 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to give 4-{4-chloro-2-[(2,4-dichlorophenyl)amino]-7-(1-ethylpropyl)-1H-benzimidazol-1-yl}butan-1-ol, which was subjected for example without further purification.

Workup

  1. temperaturethe mixture was refluxed for 2 hr
  2. customthe reaction mixture was quenched with methanol (0.5 mL)
  3. concentrationconcentrated to dryness
  4. customThe residue was partitioned between ethyl acetate (10 mL) and water (5 mL)
  5. extractionThe aqueous layer was extracted with ethyl acetate (10 mL×3)
  6. washwashed with brine (15 mL)
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-881168743f8d48669ca6ec5a1b2a6b21
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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