Potassium Carbonate → HCID 59004597, compound

HRID 1668438Notes

Reaction equation

HRID 1668438 reaction equation
[CH2:1]([C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][C:13]([N+:17]([O-:19])=[O:18])=[CH:12][CH:11]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.Cl[CH2:22][CH2:23][CH:24]1[CH2:28][CH2:27][CH2:26][N:25]1[CH3:29].C(=O)([O-])[O-].[K+].[K+]>>[CH2:1]([C:8]1[N:9]([CH2:22][CH2:23][CH:24]2[CH2:28][CH2:27][CH2:26][N:25]2[CH3:29])[C:10]2[C:15]([CH:16]=1)=[CH:14][C:13]([N+:17]([O-:19])=[O:18])=[CH:12][CH:11]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 3017050Pyrrolidine, 2-(2-chloroethyl)-1-methyl-, hydrochloride (1:1)HCID 59004662HCID 59004662, compound

Product 1

HCID 59004597HCID 59004597, compoundYield 63.9%

Conditions

Temperature
65 °C

Procedure

Compound 3 (165 mg, 0.654 mmol), 2-(2-chloroethyl)-1-methylpyrrolidine hydrochloride (132.4 mg, 0.719 mmol), and powdered potassium carbonate (271.2 mg, 1.962 mmol) were placed in an argon-purged flask. DMF (5 mL, Aldrich sure seal™) was added and the mixture heated to 65° C. in an oil bath for 20 hours. The solution was cooled to room temperature and diluted with water (10 mL) and ethyl acetate (25 mL). The layers were separated and the aqueous phase extracted with ethyl acetate (2×25 mL). The organic extracts were combined, washed with brine (2×10 mL) and dried over magnesium sulfate. The sample was filtered, concentrated, and the resultant crude product purified using dry silica gel column chromatography eluting with 15-20 mL portions of solvent system (2M NH3 in methanol:CH2Cl2, 5:95) to afford a yellow solid 4 (152 mg, 63.9%); 1H NMR (CDCl3) δ 8.50 (d, 1H, J=2.2 Hz), 8.07 (dd, 1H, J=2.2, 9.0 Hz), 7.36-7.17 (m, 6H), 6.44 (s, 1H), 4.16 (d, 2H, J=3.0 Hz), 4.10-3.97 (m, 2H), 3.06 (t, 1H, J=7.1 Hz), 2.21 (s, 3H), 2.15-2.00 (2×m, 2H), 1.97-1.55 (m, 5H), 1.53-1.40 (m, 1H); ESI-MS (m/z, %): 364 (M+1, 100%).

Workup

  1. custompurged flask
  2. additionDMF (5 mL, Aldrich sure seal™) was added
  3. temperatureThe solution was cooled to room temperature
  4. additiondiluted with water (10 mL) and ethyl acetate (25 mL)
  5. customThe layers were separated
  6. extractionthe aqueous phase extracted with ethyl acetate (2×25 mL)
  7. washwashed with brine (2×10 mL)
  8. dry with materialdried over magnesium sulfate
  9. filtrationThe sample was filtered
  10. concentrationconcentrated
  11. customthe resultant crude product purified
  12. washeluting with 15-20 mL portions of solvent system (2M NH3 in methanol:CH2Cl2, 5:95)

Sources & evidence

ORD record
ord-4db0eab1b17247d4b9097340530981d2
Source dataset
uspto-grants-2011_08
Patent number
US07989447B2

Reaction notes

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