Dimethylformamide dimethyl acetal → HCID 53773584, compound

HRID 2287440Notes

Reaction equation

HRID 2287440 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[NH:18][C:19]([C:32]3[CH:37]=[CH:36][N:35]=[C:34]([F:38])[CH:33]=3)=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=3)[N:21]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:39]OC(OC)N(C)C>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[N:18]([CH3:39])[C:19]([C:32]3[CH:37]=[CH:36][N:35]=[C:34]([F:38])[CH:33]=3)=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:29])([F:30])[F:31])[CH:23]=3)[N:21]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 15399110HCID 15399110, compound

Product 1

HCID 53773584HCID 53773584, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To a stirring solution of 4-[5-(2-fluoropyridin-4-yl)-4-(3-trifluoromethylphenyl)1H-imidazol-2-yl]-piperidine-1-carboxylic acid benzyl ester (13.1 g, 0.025 mmole) in toluene (130 mL) was added N,N-dimethylformamide dimethyl acetal (13.1 mL). This mixture was heated to 120° C. under argon for 28 hours. The reaction was cooled, concentrated in vacuo, poured into a saturated aqueous solution of sodium bicarbonate (300 mL) which was extracted with ethyl acetate (1×1 L, 2×300 mL). The organic extracts were combined, washed with water (300 mL), brine (300 mL), dried over anhydrous sodium sulfate and concentrated to an oil. The oil was dissolved in methylene chloride (5 mL) and chromatographed on silica using 2% acetone/methylene chloride to give upon concentration of the product containing fractions the title compound 2.00 g.

Workup

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated in vacuo
  3. additionpoured into a saturated aqueous solution of sodium bicarbonate (300 mL) which
  4. extractionwas extracted with ethyl acetate (1×1 L, 2×300 mL)
  5. washwashed with water (300 mL), brine (300 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated to an oil
  8. dissolutionThe oil was dissolved in methylene chloride (5 mL)
  9. customchromatographed on silica using 2% acetone/methylene chloride
  10. customto give upon concentration of the product

Sources & evidence

ORD record
ord-65179ebe725f4167a83f6ede7711bb0e
Source dataset
uspto-grants-2000_07
Patent number
US06083949

Reaction notes

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