Lithium borohydride → HCID 58012359, compound

HRID 1698574Notes

Reaction equation

HRID 1698574 reaction equation
C([O:4][C:5](=O)[CH2:6][N:7]1[C:11]2[C:12]([CH:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[CH:13][CH:14]=[C:15]([Cl:16])[C:10]=2[N:9]=[C:8]1[NH:22][C:23]1[C:28]([CH3:29])=[CH:27][C:26]([Cl:30])=[CH:25][C:24]=1[O:31][CH3:32])(C)C.[BH4-].[Li+]>O1CCCC1.O>[Cl:16][C:15]1[C:10]2[N:9]=[C:8]([NH:22][C:23]3[C:28]([CH3:29])=[CH:27][C:26]([Cl:30])=[CH:25][C:24]=3[O:31][CH3:32])[N:7]([CH2:6][CH2:5][OH:4])[C:11]=2[C:12]([CH:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 58012354HCID 58012354, compound

Product 1

HCID 58012359HCID 58012359, compoundYield 62.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of isopropyl[4-chloro-2-[(4-chloro-2-methoxy-6-methylphenyl)amino]-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]acetate (453 mg, 0.920 mmol) in tetrahydrofuran (5 mL) was added lithium tetrahydroborate (60 mg, 2.76 mmol), and the mixture was refluxed for 2 hours. After cooling, the reaction mixture was diluted with water and extracted with ethyl acetate (X2). The combined organic layer was washed with brine (X1), dried over sodium sulfate and concentrated in vacuo. The residual solid was recrystallized with ethyl acetate-n-hexane to give 250 mg (0.573 mmol, 62.3%) of the title compound as a colorless crystal. The filtrate was concentrated in vacuo, and the residual solid was recrystallized with ethyl acetate-hexane to give 91 mg (0.209 mmol, 22.7%) of the title compound as a colorless crystal.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate (X2)
  4. washThe combined organic layer was washed with brine (X1)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residual solid was recrystallized with ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-c66c115ebabc40cd8f52c1c70a1dacd5
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

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