Cyclopentylamine → HCID 10276682, compound

HRID 1796561Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]2[N:9]=[C:10]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[C:11]([C:12]3[CH:17]=[CH:16][N:15]=[C:14]([S:18][CH3:19])[N:13]=3)=[C:4]2[CH:3]=1.C(OCC)(=O)C.[CH:34]1([NH2:39])[CH2:38][CH2:37][CH2:36][CH2:35]1>>[Cl:1][C:2]1[CH:7]=[C:6]([NH:39][CH:34]2[CH2:38][CH2:37][CH2:36][CH2:35]2)[N:5]2[N:9]=[C:10]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[C:11]([C:12]3[CH:17]=[CH:16][N:15]=[C:14]([S:18][CH3:19])[N:13]=3)=[C:4]2[CH:3]=1

Participants

Reactant 3

HCID 2906Cyclopentylamine

HCID 8857Ethyl Acetate

HCID 10158906HCID 10158906, compound

Product 1

HCID 10276682HCID 10276682, compoundYield 85%

Procedure

A solution of 5,7-dichloro-2-(4-methoxyphenyl)-3-[2-(methylsulfanyl)-4-pyrimidinyl]pyrazolo[1,5-a]pyridine (148 mg, 0.35 mmol) in cyclopentylamine (5 mL) was heated at 80° C. for 3 hours. After cooling to room temperature, ethyl acetate was added to the reaction mixture. The organic phase was washed with water and brine, then dried over magnesium sulfate. Filtration and concentration followed by chromatography (4:1 hexanes/ethyl acetate) gave N-{5-chloro-2-(4-methoxyphenyl)-3-[2-(methylsulfanyl)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-7-yl}-N-cyclopentylamine (141 mg, 85%) as a yellow foam. 1H NMR (CDCl3) δ 8.15 (d, 1H), 7.84 (d, 1H), 7.51 (d, 2H), 6.99 (d, 2H), 6.65 (d, 1H), 6.09 (d, 1H), 6.02 (d, 1H), 3.96 (m, 1H), 3.88 (s, 3H), 2.63 (s, 3H), 2.15 (m, 2H), 1.81–1.69 (m, 6H). MS m/z 466 (M+1).

Workup

washThe organic phase was washed with water and brine
dry with materialdried over magnesium sulfate
filtrationFiltration and concentration

Sources & evidence

ORD record: ord-18a78477b53b4ab2808dc0e53bc1aeee
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07030134B2

Reaction notes

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