Acetic Acid → HCID 10111242, compound

HRID 1745902Notes

Reaction equation

HRID 1745902 reaction equation
[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]2[N:7]([C:10]3[CH:19]=[CH:18][C:17]4[C:12](=[C:13]([C:20]5[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][CH:21]=5)[CH:14]=[CH:15][CH:16]=4)[N:11]=3)[CH:8]=[N:9][C:5]=2[CH:4]=1.CN.C(O)(=O)C.[C:36]([BH3-])#[N:37].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]2[N:7]([C:10]3[CH:19]=[CH:18][C:17]4[C:12](=[C:13]([C:20]5[CH:27]=[CH:26][C:23]([CH2:24][NH:37][CH3:36])=[CH:22][CH:21]=5)[CH:14]=[CH:15][CH:16]=4)[N:11]=3)[CH:8]=[N:9][C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6329MethylamineHCID 5003444Sodium cyanoborohydrideHCID 22227052HCID 22227052, compound

Product 1

HCID 10111242HCID 10111242, compoundYield 174.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

4-[2-(5-Methoxy-benzoimidazol-1-yl)-quinolin-8-yl]-benzaldehyde 5A (120 mg, 0.32 mMol) was dissolved in 2 mL of methanol under an atmosphere of dry N2. To this solution was added 800 μL of a solution of 2.0 M methylamine in methanol and then acetic acid (AcOH) was added dropwise until the pH of the solution was ˜5. To this solution was added (42 mg, 0.64 mMol) sodium cyanoborohydride (NaCNBH3) and the reaction mixture was stirred at ambient temperature overnight. The reaction mixture was then concentrated under vacuum and subsequently partitioned between DCM and 0.1 N aqueous NaOH. The DCM layer was washed again with 0.1 N aqueous NaOH, then dried over MgSO4, filtered and concentrated under vacuum to give 220 mg of a green residue. The residue was chromatographed on flash silica gel eluting with a gradient DCM/MeOH (595) to DCM/MeOH (15/85) to DCM/MeOH/NH4OH (1584.50.5) to give 50 mg of a white solid of the title compound 5.

Workup

  1. concentrationThe reaction mixture was then concentrated under vacuum
  2. customsubsequently partitioned between DCM and 0.1 N aqueous NaOH
  3. washThe DCM layer was washed again with 0.1 N aqueous NaOH
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-136150a2970348738784e3324ce49322
Source dataset
uspto-grants-2006_03
Patent number
US07019147B1

Reaction notes

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