Potassium Carbonate → N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-2-(imidazo[1,2-a]pyridin-2-ylmethoxy)pyrimidine-5-carboxamide

HRID 403044Notes

Reaction equation

HRID 403044 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[CH:8]=[CH:9][C:10]([CH3:26])=[C:11]([NH:13][C:14]([C:16]3[CH:17]=[N:18][C:19](S(C)(=O)=O)=[N:20][CH:21]=3)=[O:15])[CH:12]=2)=[O:6])[CH2:3][CH2:2]1.[N:27]1[C:28]([CH2:36][OH:37])=[CH:29][N:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=12.C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[CH:1]1([NH:4][C:5]([C:7]2[CH:8]=[CH:9][C:10]([CH3:26])=[C:11]([NH:13][C:14]([C:16]3[CH:17]=[N:18][C:19]([O:37][CH2:36][C:28]4[N:27]=[C:31]5[CH:32]=[CH:33][CH:34]=[CH:35][N:30]5[CH:29]=4)=[N:20][CH:21]=3)=[O:15])[CH:12]=2)=[O:6])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2795540Imidazo[1,2-a]pyridin-2-ylmethanolHCID 66630813N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-2-(methylsulfonyl)pyrimidine-5-carboxamide

Product 1

HCID 11396588N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-2-(imidazo[1,2-a]pyridin-2-ylmethoxy)pyrimidine-5-carboxamideYield 23.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
67 °C

Procedure

A mixture of N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-2-(methylsulfonyl)pyrimidine-5-carboxamide (120 mg, 0.32 mmol), imidazo[1,2-a]pyridine-2-methanol (48 mg, 0.32 mmol) and potassium carbonate (44 mg, 0.32 mmol) in THF (5 mL) was heated to 67° C. for 3.5 h. The mixture was cooled to room temperature and partitioned between DCM and water and the layers separated. The aqueous layer was extracted with DCM and the combined organic extracts dried (MgSO4), filtered and concentrated at reduced pressure to give a yellow oil. This material was purified by silica column chromatography, eluting with a gradient of 0 to 8% methanol in DCM to give the title compound as a white solid (33 mg, 23%); NMR Spectrum: (DMSOd6) 0.57 (m, 2H), 0.67 (m, 2H), 2.27 (s, 3H), 2.83 (m, 1H), 5.70 (s, 2H), 7.26 (t, 1H), 7.35 (d, 1H), 7.66 (m, 2H), 7.78 (d, 1H), 7.83 (d, 1H), 8.30 (s, 1H), 8.38 (d, 1H), 8.75 (d, 1H), 9.17 (s, 2H), 10.16 (s, 1H); Mass Spectrum: m-H− 441, 443.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. custompartitioned between DCM and water
  3. customthe layers separated
  4. extractionThe aqueous layer was extracted with DCM
  5. dry with materialthe combined organic extracts dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated at reduced pressure
  8. customto give a yellow oil
  9. customThis material was purified by silica column chromatography
  10. washeluting with a gradient of 0 to 8% methanol in DCM

Sources & evidence

ORD record
ord-fff50a570a654533aad4415631b73074
Source dataset
uspto-grants-2014_06
Patent number
US08742124B2

Reaction notes

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