Acetonitrile → HCID 25269871, compound

HRID 1672537Notes

Reaction equation

HRID 1672537 reaction equation
Cl[C:2]1[O:3][C:4]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[C:5]([CH3:7])[N:6]=1.[C:16](#[N:18])[CH3:17]>Cl>[CH3:15][O:14][C:11]1[CH:12]=[CH:13][C:8]([C:4]2[O:3][C:2]([NH:18][C:16]3[CH:13]=[CH:12][CH:11]=[C:10]4[C:17]=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

4

Reactant 2

HCID 6342AcetonitrileHCID 66696767HCID 66696767, compound

Product 1

HCID 25269871HCID 25269871, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Procedure

A mixture of Example 14D (0.840 g, 3.76 mmol) and Example 1A (1.04 g, 3.76 mmol) in acetonitrile (19 mL) was heated in a microwave reactor at 150° C. for 20 minutes. Two drops of aqueous concentrated HCl were added and the reaction was reheated in the microwave to 150° C. for 20 min. The volatiles were evaporated and the crude material was dissolved in tetrahydrofuran (20 mL), followed by addition of 10 mL 6N HCl. The mixture was stirred overnight at ambient temperature, then diluted with ethyl acetate. The organic phase was washed with water, brine, dried over Na2SO4, and concentrated in vacuo. The crude product was purified by chromatography on silica gel using methanol/CH2Cl2 as eluent (2% to 20%), followed by triturating with diethyl ether to afford 122 mg (9% yield) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 8.89 (s, 1H), 7.60 (d, J=7.93 Hz, 1H), 7.42 (d, J=9.12 Hz, 2H), 7.04 (m, 3H), 6.81 (d, J=7.54 Hz, 1H), 4.80 (d, J=3.97 Hz, 1H), 3.92 (bs, 1H), 3.78 (s, 3H), 2.90 (m, 2H), 2.75 (m, 1H), 2.22 (s, 3H), 1.87 (bs, 1H), 1.62 (bs, 1H). MS (ESI) m/z 350 (M+H)+.

Workup

  1. customwas heated in a microwave reactor at 150° C. for 20 minutes
  2. customThe volatiles were evaporated
  3. dissolutionthe crude material was dissolved in tetrahydrofuran (20 mL)
  4. additionfollowed by addition of 10 mL 6N HCl
  5. additiondiluted with ethyl acetate
  6. washThe organic phase was washed with water, brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by chromatography on silica gel
  10. customby triturating with diethyl ether

Sources & evidence

ORD record
ord-709987076df742648e77ebb2c558ebc8
Source dataset
uspto-grants-2011_08
Patent number
US07998993B2

Reaction notes

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