Potassium Carbonate → 4-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamine

HRID 1373803Notes

Reaction equation

HRID 1373803 reaction equation
[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[C:10]([C:11](=O)[C:12]#[CH:13])=[C:6]2[CH:5]=[CH:4][CH:3]=1.Cl.[CH:23]1([NH:28][C:29]([NH2:31])=[NH:30])[CH2:27][CH2:26][CH2:25][CH2:24]1.C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O>[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[C:10]([C:11]3[CH:12]=[CH:13][N:31]=[C:29]([NH:28][CH:23]4[CH2:27][CH2:26][CH2:25][CH2:24]4)[N:30]=3)=[C:6]2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 219486831-[7-Chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-propyn-1-oneHCID 178479367HCID 178479367, compound

Product 1

HCID 102728224-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamineYield 44%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

In a similar manner as described in Example 7 1-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-2-propyn-1-one (210 mg, 0.70 mmol), cyclopentylguanidine hydrochloride (291 mg, 2.1 mmol), and potassium carbonate (345 mg, 2.1 mmol) were heated at 120° C. for 1.5 hours in 1-methyl-2-pyrrolidinone (8 mL) to form 4-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamine (125 mg, 44%) as a white foam. 1H NMR (CDCl3) δ 8.42 (d, 1H), 8.09 (d, 1H), 7.67 (dd, 2H), 7.30 (m, 1H), 7.17 (t, 2H), 7.06 (d, 1H), 6.33 (d, 1H), 5.30 (d, 1H), 4.35 (m, 1H), 2.18–2.05 (m, 2H), 1.84–1.52 (m, 6H); 19F NMR (CDCl3) δ −112.78; MS m/z 408 (M+1).

Sources & evidence

ORD record
ord-2c0f546cddb540dc9e4e1161f382ec9c
Source dataset
uspto-grants-2007_01
Patent number
US07163940B2

Reaction notes

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