Acetic Acid → HCID 69479566, compound

HRID 856273Notes

Reaction equation

HRID 856273 reaction equation
[F:1][C:2]([F:31])([F:30])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH:11]2[CH2:16][CH2:15][N:14]([CH2:17][C@:18]3([CH3:29])[O:22][C:21]4=[N:23][C:24]([N+:26]([O-:28])=[O:27])=[CH:25][N:20]4[CH2:19]3)[CH2:13][CH2:12]2)=[CH:6][CH:5]=1.C=O.[B-][C:35]#N.[Na+].C(O)(=O)C.C(=O)([O-])O.[Na+]>CO>[CH3:29][C@@:18]1([CH2:17][N:14]2[CH2:15][CH2:16][CH:11]([N:10]([CH3:35])[C:7]3[CH:8]=[CH:9][C:4]([O:3][C:2]([F:1])([F:30])[F:31])=[CH:5][CH:6]=3)[CH2:12][CH2:13]2)[O:22][C:21]2=[N:23][C:24]([N+:26]([O-:28])=[O:27])=[CH:25][N:20]2[CH2:19]1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 20587905Sodium cyanoborohydride [MI]HCID 69479167HCID 69479167, compound

Product 1

HCID 69479566HCID 69479566, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(S)-2-[4-(4-Trifluoromethoxyphenyl)aminopiperidin-1-yl]methyl-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole prepared in Example 282 (400 mg, 0.90 mmol) was dissolved in methanol (10 ml). To the solution, a 37% formaldehyde solution (0.13 ml, 4.52 mmol), sodium cyanotrihydroborate (170 mg, 2.71 mmol) and acetic acid (0.17 ml, 2.71 mmol) were added followed by stirring at room temperature for 30 minutes. The reaction mixture was poured into a saturated sodium hydrogencarbonate solution and extracted with methylene chloride. The organic phase was dried over magnesium sulfate and then filtered. The resulting filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/methanol=100/1) and recrystallized from methylene chloride-diisopropyl ether to afford (S)-N-[1-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperidin-4-yl]-N-methyl-4-trifluoromethoxyaniline (309 mg, yield 78%) as a light yellow crystals.

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe resulting filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (methylene chloride/methanol=100/1)
  6. customrecrystallized from methylene chloride-diisopropyl ether

Sources & evidence

ORD record
ord-5882d78cf89a434686f7e3a6ff66efd8
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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