Acetonitrile → HCID 25269870, compound

HRID 1672536Notes

Reaction equation

HRID 1672536 reaction equation
Cl[C:2]1[O:3][C:4]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)=[C:5]([CH3:7])[N:6]=1.[C:15](#[N:17])[CH3:16]>>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([C:4]2[O:3][C:2]([NH:17][C:15]3[CH:13]=[CH:12][CH:11]=[C:10]4[C:16]=3[CH2:5][CH:4]([OH:3])[CH2:8][CH2:9]4)=[N:6][C:5]=2[CH3:7])=[CH:9][CH:10]=1

Participants

3

Reactant 2

HCID 6342AcetonitrileHCID 66696762HCID 66696762, compound

Product 1

HCID 25269870HCID 25269870, compoundYield 17%

Procedure

A mixture of Example 13D (540 mg, 2.37 mmol) and Example 1A (657 mg, 2.37 mmol) in acetonitrile (6 mL) was heated in a microwave reactor at 150° C. for 20 minutes. The reaction was cooled and the solvent was evaporated. The residue was dissolved in tetrahydrofuran (20 mL) and 10 mL 6N HCl and the mixture was stirred several hours at ambient temperature. The mixture was then diluted with ethyl acetate, and the organic phase was washed with water, brine, dried over Na2SO4, filtered, and evaporated. The crude product was chromatographed on silica gel using methanol/CH2Cl2 as eluent (2% to 20%) that gave a solid that was further purified by trituration to afford 143 mg (17% yield) of the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 9.05 (s, 1H) 7.56 (d, J=7.12 Hz, 1H), 7.48 (s, 4H), 7.10 (t, J=7.80 Hz, 1H), 6.84 (d, J=7.12 Hz, 1H), 4.79 (d, J=3.73 Hz, 1H), 3.92 (bs, 1H), 2.97 (m, 2H), 2.68 (m, 1H), 2.26 (s, 3H), 1.87 (bs, 1H), 1.61 (bs, 1H). MS (ESI+) m/z 354 (M+H)+.

Workup

  1. customwas heated in a microwave reactor at 150° C. for 20 minutes
  2. temperatureThe reaction was cooled
  3. customthe solvent was evaporated
  4. dissolutionThe residue was dissolved in tetrahydrofuran (20 mL)
  5. additionThe mixture was then diluted with ethyl acetate
  6. washthe organic phase was washed with water, brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated
  10. customThe crude product was chromatographed on silica gel
  11. customgave a solid
  12. customthat was further purified by trituration

Sources & evidence

ORD record
ord-dfe1cf5601544242983efb2c4007fea9
Source dataset
uspto-grants-2011_08
Patent number
US07998993B2

Reaction notes

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