Lithium borohydride → HCID 68770584, compound

HRID 1628402Notes

Reaction equation

HRID 1628402 reaction equation
[BH4-].[Li+].[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[NH:11][C:12]1[N:16]([CH2:17][CH2:18][C:19](OCC)=[O:20])[C:15]2[C:24]([N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])=[CH:25][CH:26]=[CH:27][C:14]=2[N:13]=1>O1CCCC1.[Cl-].[NH4+].C(=O)([O-])O.[Na+]>[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[NH:11][C:12]1[N:16]([CH2:17][CH2:18][CH2:19][OH:20])[C:15]2[C:24]([N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])=[CH:25][CH:26]=[CH:27][C:14]=2[N:13]=1

Participants

6

Reactant 2

HCID 4148881Lithium borohydrideHCID 68761561HCID 68761561, compound

Product 1

HCID 68770584HCID 68770584, compoundYield 25.4%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of lithium borohydride (22.5 mg, 1.03 mmol) in tetrahydrofuran (3.5 mL) was added ethyl 3-[2-[(2,4-dichlorophenyl)amino]-7-(diethylamino)-1H-benzimidazol-1-yl]propanoate (Reference Example 28; 155 mg, 0.345 mmol) at 0° C. After the resultant mixture was stirred at room temperature for 20 hr, the mixture was diluted with aqueous ammonium chloride at 0° C. and stirred at 0° C. for 30 min. The resultant mixture was diluted with aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 25% ethyl acetate/n-hexane mixture to give the title compound as a solid (35.7 mg, 0.0876 mmol, 25%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel eluting with a 25% ethyl acetate/n-hexane mixture

Sources & evidence

ORD record
ord-1be540d0f4b44ff9858403443c44adfa
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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