Sodium borohydride → HCID 59170971, compound

HRID 2247548Notes

Reaction equation

HRID 2247548 reaction equation
[BH4-].[Na+].[CH:3]([C:5]1[CH:6]=[C:7](/[CH:16]=[CH:17]/[C:18]([NH:20][CH:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:23][CH2:22]2)=[O:19])[CH:8]=[CH:9][C:10]=1[N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1)=[O:4]>C(O)C>[OH:4][CH2:3][C:5]1[CH:6]=[C:7](/[CH:16]=[CH:17]/[C:18]([NH:20][CH:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:23][CH2:22]2)=[O:19])[CH:8]=[CH:9][C:10]=1[N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59170865HCID 59170865, compound

Product 1

HCID 59170971HCID 59170971, compoundYield 10.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (2 mg) is added to an ethanol (1 mL) solution of (E)-3-(3-formyl-4-(1H-imidazol-1-yl)phenyl)-N-indan-1-ylacrylamide (17 mg) obtained in Example 437 and the reaction mixture was agitated for 30 minutes at room temperature. After the reaction solution was concentrated under reduced pressure, water and ethyl acetate were added to the residue, and the organic layer was partitioned. The organic layer was washed with a saturated saline solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Carrier: Chromatorex™ NH, elution solvent: methanol-ethyl acetate system), and 1.8 mg of the title compound was obtained.

Workup

  1. concentrationAfter the reaction solution was concentrated under reduced pressure, water and ethyl acetate
  2. additionwere added to the residue
  3. customthe organic layer was partitioned
  4. washThe organic layer was washed with a saturated saline solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (Carrier: Chromatorex™ NH, elution solvent: methanol-ethyl acetate system)

Sources & evidence

ORD record
ord-460d334a5b684ff8a8d170ee515c3501
Source dataset
uspto-grants-2010_03
Patent number
US07687640B2

Reaction notes

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