Water → HCID 68773849, compound

HRID 1628546Notes

Reaction equation

HRID 1628546 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([NH:11][C:12]3[C:13]([CH3:18])=[N:14][O:15][C:16]=3[CH3:17])[N:7]([CH2:19][CH2:20][CH2:21][C:22](OCC)=[O:23])[C:6]=2[C:5]([CH:27]([CH2:30][CH3:31])[CH2:28][CH3:29])=[CH:4][CH:3]=1.[BH4-].[Li+].O>O1CCCC1>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([NH:11][C:12]3[C:13]([CH3:18])=[N:14][O:15][C:16]=3[CH3:17])[N:7]([CH2:19][CH2:20][CH2:21][CH2:22][OH:23])[C:6]=2[C:5]([CH:27]([CH2:30][CH3:31])[CH2:28][CH3:29])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydride2×HCID 68764632HCID 68764632, compound

Product 1

HCID 68773849HCID 68773849, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-{4-chloro-2-[(3,5-dimethylisoxazol-4-yl)amino]-7-(1-ethylpropyl)-1H-benzimidazol-1-yl}butanoate (400 mg, 0.90 mmol) in tetrahydrofuran (5 mL) was added lithium borohydride (62 mg, 2.68 mmol) portionwise at 0° C. The mixture was warmed to room temperature and stirred for 16 hr. Additional lithium borohydride (62 mg, 2.68 mmol) was added and the mixture was warmed to 50° C. for 4 hr. Water was added and the mixture was extracted with ethyl acetate. Organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with a 50-100% ethyl acetate/n-hexane gradient mixture followed by recrystallization from ethyl acetate/n-hexane to give the title compound (193 mg, 0.47 mmol, 53%) as a colorless solid.

Workup

  1. temperaturethe mixture was warmed to 50° C. for 4 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washOrganic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel eluting with a 50-100% ethyl acetate/n-hexane gradient mixture
  7. customfollowed by recrystallization from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-660ed648412c4c2187b2ec0ab7c18c06
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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