Acetic Acid → HCID 66887136, compound

HRID 1677826Notes

Reaction equation

HRID 1677826 reaction equation
[CH2:1]([N:8]1[C:12]2[CH:13]=[CH:14][C:15]([CH3:17])=[CH:16][C:11]=2[N:10]=[C:9]1[CH:18]([NH2:22])[CH:19]([CH3:21])[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:23]=[C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26](=[O:33])[N:25]1[CH2:34][CH2:35][CH:36]=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][C:15]([CH3:17])=[CH:16][C:11]=2[N:10]=[C:9]1[CH:18]([NH:22][CH2:36][CH2:35][CH2:34][N:25]1[C:26](=[O:33])[C:27]2[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:24]1=[O:23])[CH:19]([CH3:20])[CH3:21])[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 66885830HCID 66885830, compound

Product 1

HCID 66887136HCID 66887136, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(1-benzyl-5-methyl-1H-benzimidazol-2-yl)-2-methyl-propylamine (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 min., acetic acid (34 μl, 0.56 mmol) was added to the reaction mixture. The mixture was stirred at room temperature for 1 h. 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 crude material that was used in step 7.

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 crude material that

Sources & evidence

ORD record
ord-08fd96b49db84a2d8acf184b40e505cb
Source dataset
uspto-grants-2011_08
Patent number
US08008335B2

Reaction notes

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