Cyclopentylamine → HCID 10276682, compound

HRID 1062879Notes

Reaction equation

HRID 1062879 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

4

Reactant 3

HCID 2906CyclopentylamineHCID 8857Ethyl AcetateHCID 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

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

Sources & evidence

ORD record
ord-20a27cf9ed6745c4808ccc6416f8ab8a
Source dataset
uspto-grants-2005_11
Patent number
US06962914B2

Reaction notes

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