Sodium ethoxide → 4-[7-Chloro-2-(3-methyl-2-furyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamine

HRID 1269069Notes

Reaction equation

HRID 1269069 reaction equation
CC[O-].[Na+].Cl.[CH:6]1([NH:11][C:12]([NH2:14])=[NH:13])[CH2:10][CH2:9][CH2:8][CH2:7]1.[Cl:15][C:16]1[N:21]2[N:22]=[C:23]([C:29]3[O:30][CH:31]=[CH:32][C:33]=3[CH3:34])[C:24]([C:25](=O)[C:26]#[CH:27])=[C:20]2[CH:19]=[CH:18][CH:17]=1>C(O)C>[Cl:15][C:16]1[N:21]2[N:22]=[C:23]([C:29]3[O:30][CH:31]=[CH:32][C:33]=3[CH3:34])[C:24]([C:25]3[CH:26]=[CH:27][N:14]=[C:12]([NH:11][CH:6]4[CH2:10][CH2:9][CH2:8][CH2:7]4)[N:13]=3)=[C:20]2[CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 184465971-[7-Chloro-2-(3-methyl-2-furyl)pyrazolo[1,5-a]pyridin-3-yl]-2-propyn-1-oneHCID 178479367HCID 178479367, compound

Product 1

HCID 111768674-[7-Chloro-2-(3-methyl-2-furyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamineYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium ethylate solution (21% T, 0.5 mL, 1.43 mmol) was added to ethanol followed by cyclopentylguanidine hydrochloride (323 mg, 1.98 mmol). The mixture was stirred at room temperature for 30 minutes. 1-[7-Chloro-2-(3-methyl-2-furyl)pyrazolo[1,5-a]pyridin-3-yl]-2-propyn-1-one (313 mg, 1.10 mmol) was added to the resultant solution and stirred at room temperature for 15 hours. The reaction mixture was concentrated. Ethyl acetate and water were added to the residue. The phases were separated, the organic phase dried (magnesium sulfate), filtered and concentrated. The residue was recrystallized from ethyl acetate. 4-[7-Chloro-2-(3-methyl-2-furyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamine (280 mg, 65%) was obtained as a yellow solid. 1H-NMR (CDCl3): δ 8.50 (d, 1H), 8.15 (d, 1H), 7.49 (d, 1H), 7.27 (t, 1H), 7.06 (d, 1H), 6.41 (d, 1H), 6.36 (d, 1H), 5.10 (d, 1H), 4.35 (m, 1H), 2.12 (s, 3H), 2.08 (m, 2H), 1.78–1.53 (m, 6H). MS m/z 394 (M+1).

Workup

  1. stirringstirred at room temperature for 15 hours
  2. concentrationThe reaction mixture was concentrated
  3. additionEthyl acetate and water were added to the residue
  4. customThe phases were separated
  5. dry with materialthe organic phase dried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-2dca8a713af54b93ae23f86125a1076a
Source dataset
uspto-grants-2007_04
Patent number
US07199120B2

Reaction notes

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