Water → HCID 69479455, compound

HRID 856274Notes

Reaction equation

HRID 856274 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(N(CC)CC)C.[C:39](Cl)(=[O:41])[CH3:40].O>C(Cl)Cl>[CH3:29][C@@:18]1([CH2:17][N:14]2[CH2:15][CH2:16][CH:11]([N:10]([C:7]3[CH:8]=[CH:9][C:4]([O:3][C:2]([F:1])([F:30])[F:31])=[CH:5][CH:6]=3)[C:39](=[O:41])[CH3:40])[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

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 69479167HCID 69479167, compound

Product 1

HCID 69479455HCID 69479455, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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 (153 mg, 0.35 mmol) was dissolved in methylene chloride (5 ml). To the solution, triethylamine (30 μl) and acetyl chloride (30 μl) were added followed by stirring at room temperature for 1.5 hours. The reaction mixture was poured into water 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 crystallized 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-(4-trifluoromethoxyphenyl)acetamide (82 mg, yield 49%) as a white powder.

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. customcrystallized from methylene chloride-diisopropyl ether

Sources & evidence

ORD record
ord-f4727b6a5c2b4ab5b1d6f1264e771c3d
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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