Cyclopentylamine → HCID 18446642, compound

HRID 1269055Notes

Reaction equation

HRID 1269055 reaction equation
F[C:2]1[CH:7]=[C:6]([C:8]2[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:23][CH:24]([CH3:26])[CH3:25])[N:18]=3)=[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)[CH:5]=[CH:4][N:3]=1.[CH:27]1([NH2:32])[CH2:31][CH2:30][CH2:29][CH2:28]1>>[CH:27]1([NH:32][C:2]2[CH:7]=[C:6]([C:8]3[C:16]([C:17]4[CH:22]=[CH:21][N:20]=[C:19]([NH:23][CH:24]([CH3:25])[CH3:26])[N:18]=4)=[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][N:10]4[N:9]=3)[CH:5]=[CH:4][N:3]=2)[CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

3

Reactant 2

HCID 2906CyclopentylamineHCID 10308898HCID 10308898, compound

Product 1

HCID 18446642HCID 18446642, compoundYield 640%

Procedure

A solution of crude 4-[2-(2-fluoro-4-pyridinyl)pyrazolo[1,5-a]pyridin-3-yl]-N-isopropyl-2-pyrimidinamine (204 mg, 0.586 mmol) in cyclopentylamine (2 mL, 20.3 mmol) was heated at 135° C. in a sealed glass tube for 16 hours. The reaction mixture was cooled and the excess cyclopentylamine was removed in vacuo. The resultant residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The organic layer was washed with brine and dried over magnesium sulfate. Filtration and concentration, followed by flash chromatography (1:1 hexanes:ethyl acetate to 100% ethyl acetate) provided N-cyclopentyl-N-(4-{3-[2-(isopropylamino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-2-yl}-2-pyridinyl)amine (155 mg, 640%). Rf 0.16 (1:2 hexanes:ethyl acetate); 1H NMR (CDCl3) δ 8.49 (d, 1H), 8.39 (d, 1H), 8.13–8.08 (m, 2H), 7.29 (t, 1H), 6.89 (t, 1H), 6.80 (d, 1H), 6.63 (s, 1H), 6.46 (d, 1H), 5.23 (br, 1H), 4.86 (d, 1H), 4.21 (m, 1H), 3.93 (m, 1H), 1.95 (m, 2H), 1.70–1.42 (m, 6H), 1.27 (d, 6H); MS m/z 414 (M+1).

Workup

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

Sources & evidence

ORD record
ord-2253f8c72e8b40bea7aa39e376c617b9
Source dataset
uspto-grants-2007_04
Patent number
US07199120B2

Reaction notes

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