Acetic Acid → HCID 68564972, compound

HRID 1443626Notes

Reaction equation

HRID 1443626 reaction equation
[CH2:1]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[CH:17]([NH2:21])[CH:18]([CH3:20])[CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:22]=[C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25](=[O:32])[N:24]1[CH2:33][CH2:34][CH:35]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C(Cl)Cl>[CH2:1]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[CH:17]([NH:21][CH2:35][CH2:34][CH2:33][N:24]1[C:25](=[O:32])[C:26]2[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:23]1=[O:22])[CH:18]([CH3:19])[CH3:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 75525Phthalimide, N-(2-formylethyl)-HCID 5049666Sodium triacetoxyborohydrideHCID 45588680HCID 45588680, compound

Product 1

HCID 68564972HCID 68564972, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(1-benzyl-1H-benzimidazol-2-yl)-2-methyl-propylamine (160 mg, 0.56 mmol) and 3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionaldehyde (114 mg, 0.56 mmol) in dry DCM (3 ml) at room temperature, was added sodium triacetoxyborohydride (119 mg, 0.56 mmol). After 10 minutes, acetic acid (34 μl, 0.56 mmol) was added to the reaction mixture. The mixture was stirred at room temperature for 1 hour. The solvent was removed in vacuo and the solid was dissolved in ethyl acetate. The organic layer was washed with saturated NaHCO3, dried over MgSO4, filtered and the filtrate was concentrated in vacuo. The crude product was purified by flash chromatography to give material that was used in Example 5g.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe solid was dissolved in ethyl acetate
  3. washThe organic layer was washed with saturated NaHCO3
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe crude product was purified by flash chromatography
  8. customto give material that

Sources & evidence

ORD record
ord-1e1e979e48404e939c081ca120585047
Source dataset
uspto-grants-2010_02
Patent number
US07662581B1

Reaction notes

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