Potassium Carbonate → HCID 18446623, compound

HRID 1269074Notes

Reaction equation

HRID 1269074 reaction equation
Cl.[CH:2]1([NH:7][C:8]([NH2:10])=[NH:9])[CH2:6][CH2:5][CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].[Cl:17][C:18]1[N:23]2[N:24]=[C:25]([C:31]3[O:32][CH:33]=[CH:34][CH:35]=3)[C:26]([C:27](=O)[C:28]#[CH:29])=[C:22]2[CH:21]=[CH:20][CH:19]=1>C(O)C>[Cl:17][C:18]1[N:23]2[N:24]=[C:25]([C:31]3[O:32][CH:33]=[CH:34][CH:35]=3)[C:26]([C:27]3[CH:28]=[CH:29][N:10]=[C:8]([NH:7][CH:2]4[CH2:6][CH2:5][CH2:4][CH2:3]4)[N:9]=3)=[C:22]2[CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 18446595HCID 18446595, compoundHCID 178479367HCID 178479367, compound

Product 1

HCID 18446623HCID 18446623, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Cyclopentylguanidine hydrochloride (1.53 g, 9.38 mmol) and potassium carbonate (0.78 g. 5.63 mmol) were added to 80 mL of ethanol. The suspension was stirred at room temperature for 1 hour. 1-[7-Chloro-2-(2-furyl)pyrazolo[1,5-a]pyridin-3-yl]-2-propyn-1-one (1.27 g, 4.69 mmol) was added to the resultant solution and stirred at room temperature for 24 hours. The reaction mixture was concentrated and ethyl acetate and water were added. The phases were separated, the organic phase was dried over magnesium sulfate, filtered and concentrated. Purification by flash chromatography (3:7 ethyl acetatehexanes). gave 4-[7-Chloro-2-(2-furyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamine (520 mg, 30%) as a yellow solid. 1H NMR (CDCl3): δ 8.28 (d, 1H), 8.22 (d, 1H), 7.58 (d, 1H), 7.23 (m, 1H), 7.04 (d, 1H), 6.92 (d, 1H), 6.62 (d, 1H), 6.53 (m, 1H), 5.16 (d, 1H), 4.35 (m, 1H), 2.07 (m, 2H), 1.77–1.52 (m, 6H). MS m/z 380 (M+1).

Workup

  1. stirringstirred at room temperature for 24 hours
  2. concentrationThe reaction mixture was concentrated
  3. additionethyl acetate and water were added
  4. customThe phases were separated
  5. dry with materialthe organic phase was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by flash chromatography (3:7 ethyl acetatehexanes)

Sources & evidence

ORD record
ord-d52a4eb1c33b44c9b6b676f68d2e6ad4
Source dataset
uspto-grants-2007_04
Patent number
US07199120B2

Reaction notes

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