Acetic Acid → HCID 178420114, compound

HRID 1057308Notes

Reaction equation

HRID 1057308 reaction equation
[C:1]1([C:7]2[NH:11][C:10]([C:12]3[CH:13]=[CH:14][C:15]([N:18]4[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]4)=[N:16][CH:17]=3)=[N:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(=O)C.C(O[C:31]1(O[Si](C)(C)C)[CH2:33][CH2:32]1)C.C([BH3-])#N.[Na+]>CO>[CH:31]1([N:21]2[CH2:22][CH2:23][N:18]([C:15]3[CH:14]=[CH:13][C:12]([C:10]4[NH:9][CH:8]=[C:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)[N:11]=4)=[CH:17][N:16]=3)[CH2:19][CH2:20]2)[CH2:33][CH2:32]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 2734686(1-Ethoxycyclopropoxy)trimethylsilaneHCID 5003444Sodium cyanoborohydrideHCID 18671610HCID 18671610, compound

Product 1

HCID 178420114HCID 178420114, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(Reference: Tetrahedron Lett. 1995, 36 (41), 7399) To a solution of 1-[5-(5-phenyl-1H-imidazol-2-yl)-pyridin-2-yl]-piperazine (99 mg, 0.32 mmol) in anhydrous methanol (5 ml) under nitrogen atmosphere was added 3A molecular sieves (50 mg). This solution was stirred for 5 min, then glacial acetic acid (0.19 ml, 200 mg, 3.3 mmol, 10 equiv), (1-ethoxy-cyclopropoxy)-trimethyl-silane (0.32 ml, 281 mg, 1.62 mmol, 5 equiv), and sodium cyanoborohydride (81 mg, 1.29 mmol, 4.0 equiv) were added. The reaction was heated at reflux overnight, then cooled to room temperature. The mixture was filtered, then diluted with an aqueous solution of 1N NaOH and extracted with ethyl acetate. The combined organics were dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give the desired product (74 mg, 66%). MS m/z 346 (M++1).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux overnight
  3. filtrationThe mixture was filtered
  4. additiondiluted with an aqueous solution of 1N NaOH
  5. extractionextracted with ethyl acetate
  6. dry with materialThe combined organics were dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-caa3baacde1d425a9733f5561bfd6df1
Source dataset
uspto-grants-2003_02
Patent number
US06514966B2

Reaction notes

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