HCID 86616863, compound → HCID 10118772, compound

HRID 1373841Notes

Reaction equation

HRID 1373841 reaction equation
[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[C:10]([C:11]3[N:16]=[C:15]([NH:17][CH:18]4[CH2:22][CH2:21][CH2:20][CH2:19]4)[N:14]=[C:13]([C:23]([O:25]C)=O)[CH:12]=3)=[C:6]2[CH:5]=[CH:4][CH:3]=1>C1(N)CCCC1>[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[C:10]([C:11]3[N:16]=[C:15]([NH:17][CH:18]4[CH2:19][CH2:20][CH2:21][CH2:22]4)[N:14]=[C:13]([C:23]([NH:17][CH:18]4[CH2:22][CH2:21][CH2:20][CH2:19]4)=[O:25])[CH:12]=3)=[C:6]2[CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 86616863HCID 86616863, compound

Product 1

HCID 10118772HCID 10118772, compoundYield 139%

Reagents, catalysts & solvents 1

HCID 2906CyclopentylamineSolvent

Procedure

A solution of methyl 6-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-2-(cyclopentylamino)pyrimidine-4-carboxylate (45 mg, 0.097 mmol) in cyclopentylamine (1 mL) was heated at 85° C. in a sealed tube for 24 hours. The reaction mixture was cooled and the excess cyclopentylamine was removed in vacuo. The resulting residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The organic layer was washed with water and brine, then dried over magnesium sulfate. Filtration and concentration followed by flash chromatography (4:1 hexanes:ethyl acetate) provided 6-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-N-cyclopentyl-2-(cyclopentylamino)pyrimidine-4-carboxamide (35 mg, 70%). 1H NMR (CDCl3) δ 8.34 (d, 1H), 7.78 (br, 1H), 7.65 (m, 2H), 7.31–7.26 (m, 2H), 7.14 (t, 2H), 7.07 (d, 1H), 5.16 (br, 1H), 4.34–4.24 (m, 2H), 2.07–2.00 (m, 4H), 1.80–1.48 (m, 12H); MS m/z 519 (M+1). A portion of this material was treated with anhydrous hydrochloric acid in ether to provide a hydrochloride salt as a yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe excess cyclopentylamine was removed in vacuo
  3. customThe resulting residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-943f975a296543afa8443029ab573f81
Source dataset
uspto-grants-2007_01
Patent number
US07163940B2

Reaction notes

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