Acetic Acid → HCID 58896591, compound

HRID 2235538Notes

Reaction equation

HRID 2235538 reaction equation
[C:1]1([CH3:24])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[NH:9][C:10]1[N:14]([CH3:15])[C:13]2[C:16]([NH:20][CH2:21][CH2:22][CH3:23])=[CH:17][CH:18]=[CH:19][C:12]=2[N:11]=1.[CH:25]1([CH:28]=O)[CH2:27][CH2:26]1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH:25]1([CH2:28][N:20]([CH2:21][CH2:22][CH3:23])[C:16]2[C:13]3[N:14]([CH3:15])[C:10]([NH:9][C:2]4[C:3]([CH3:8])=[CH:4][C:5]([CH3:7])=[CH:6][C:1]=4[CH3:24])=[N:11][C:12]=3[CH:19]=[CH:18][CH:17]=2)[CH2:27][CH2:26]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 123114CyclopropanecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 86612998HCID 86612998, compound

Product 1

HCID 58896591HCID 58896591, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 0.041 g (0.13 mmol) of N2-mesityl-1-methyl-N7-propyl-1H-benzimidazole-2,7-diamine in 2 mL of methanol was added 95 μL (1.3 mmol) of cyclopropane carboxaldehyde, 200 μL of glacial acetic acid and 0.032 g (0.51 mmol) of sodium cyanoborohydride. The mixture was stirred at room temperature for 24 h. The reaction mixture was cooled to room temperature and the volatiles were removed in vacuo. The crude solid was partitioned between saturated sodium bicarbonate and dichloromethane, the organic layer was separated, dried over sodium sulfate, filtered, concentrated and purified by reverse-phase HPLC to give 0.026 g (42%) of the title compound as a colorless sticky solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe volatiles were removed in vacuo
  3. customThe crude solid was partitioned between saturated sodium bicarbonate and dichloromethane
  4. customthe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by reverse-phase HPLC

Sources & evidence

ORD record
ord-f0e72665dd08491581b894d9bc5fe6b8
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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