Potassium Carbonate → HCID 86616858, compound

HRID 1373798Notes

Reaction equation

HRID 1373798 reaction equation
[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[C:10]([C:11](=O)[C:12]#[C:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[C:6]2[CH:5]=[CH:4][CH:3]=1.Cl.[CH:29]1([NH:34][C:35]([NH2:37])=[NH:36])[CH2:33][CH2:32][CH2:31][CH2:30]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O.CCOCC>[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[C:10]([C:11]3[CH:12]=[C:13]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[N:37]=[C:35]([NH:34][CH:29]4[CH2:33][CH2:32][CH2:31][CH2:30]4)[N:36]=3)=[C:6]2[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 86616859HCID 86616859, compoundHCID 178479367HCID 178479367, compound

Product 1

HCID 86616858HCID 86616858, compoundYield 84%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-3-phenyl-2-propyn-1-one (246 mg, 0.66 mmol) in N,N-dimethylformamide (10 mL) was added N-cyclopentylguanidine hydrochloride (320 mg, 1.97 mmol) followed by solid potassium carbonate (274 mg, 1.97 mmol). The resultant mixture was heated to 75° C. for 4 hours The reaction mixture was cooled to room temperature, diluted with water and ether was added. The organic layer was washed with brine. The aqueous layer was extracted with ether and the combined organics were dried over magnesium sulfate. Filtration and concentration followed by flash chromatography (4:1, hexanes:ethyl acetate) provided 4-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-N-cyclopentyl-6-phenyl-2-pyrimidinamine (265 mg, 84%) as a solid. 1H NMR (CDCl3) δ 8.49 (d, 1H), 7.80–7.75 (m, 4H), 7.44–7.41 (m, 3H), 7.33 (m, 1H), 7.22 (t, 2H), 7.09 (d, 1H), 6.82 (s, 1H), 5.25 (d, 1H), 4.49 (m, 1H), 2.22–2.12 (m, 2H), 1.88–1.61 (m, 6H); 19F NMR (CDCl3) δ −112.89; MS m/z 484 (M+1).

Workup

  1. additionwas added
  2. washThe organic layer was washed with brine
  3. extractionThe aqueous layer was extracted with ether
  4. dry with materialthe combined organics were dried over magnesium sulfate
  5. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-bcd35eb283304abe88270966895feaa7
Source dataset
uspto-grants-2007_01
Patent number
US07163940B2

Reaction notes

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