Acetic Acid → HCID 69481699, compound

HRID 856369Notes

Reaction equation

HRID 856369 reaction equation
[CH3:1][C:2]1([CH2:13][N:14]2[CH2:20][CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]2)[O:6][C:5]2=[N:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][N:4]2[CH2:3]1.C(N(CC)CC)C.[C:35]1([C:41]2[CH:48]=[CH:47][C:44]([CH:45]=O)=[CH:43][CH:42]=2)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[B-]C#N.[Na+].C(O)(=O)C.C(=O)([O-])O.[Na+]>FC(F)(F)C(O)=O>[C:41]1([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:48]=[CH:47][C:44]([CH2:45][N:17]2[CH2:18][CH2:19][CH2:20][N:14]([CH2:13][C:2]3([CH3:1])[O:6][C:5]4=[N:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][N:4]4[CH2:3]3)[CH2:15][CH2:16]2)=[CH:43][CH:42]=1

Participants

8

Reactant 6

HCID 176Acetic AcidHCID 8471TriethylamineHCID 76689(1,1'-Biphenyl)-4-carboxaldehydeHCID 516892Sodium BicarbonateHCID 20587905Sodium cyanoborohydride [MI]HCID 23081102HCID 23081102, compound

Product 1

HCID 69481699HCID 69481699, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of tert-butyl 4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)-homopiperazin-1-carboxylate prepared in Example 645 (346 mg, 0.91 mmol) and trifluoroacetic acid (10 ml) was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in methylene chloride (10 ml). To the solution, triethylamine (0.27 ml, 1.96 mmol) was added. The solution was concentrated under reduced pressure, and the residue was dissolved in methanol (10 ml). To the solution, 4-phenylbenzaldehyde (496 mg, 2.72 mmol), sodium cyanotrihydroborate (171 mg, 2.72 mmol) and acetic acid (0.17 ml, 2.72 mmol) were added in this order followed by stirring at room temperature overnight. The reaction mixture was poured into a saturated sodium hydrogencarbonate solution, then extracted with methylene chloride. The organic phase was dried over magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=5/1) to afford 2-[4-(biphenyl-4-ylmethyl)homopiperazin-1-ylmethyl]-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole (251 mg, yield 62%) as a white powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in methylene chloride (10 ml)
  3. concentrationThe solution was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in methanol (10 ml)
  5. stirringby stirring at room temperature overnight
  6. extractionextracted with methylene chloride
  7. dry with materialThe organic phase was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under reduced pressure
  10. customthe residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-19bc7112ee82459f832bdda3f01a4174
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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