HCID 17953061, compound → HCID 10115190, compound

HRID 1373809Notes

Reaction equation

HRID 1373809 reaction equation
[CH:1]1([NH:6][C:7]2[N:12]3[N:13]=[C:14]([C:23]4[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=4)[C:15]([C:16]4[CH:21]=[CH:20][N:19]=[C:18](F)[CH:17]=4)=[C:11]3[CH:10]=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>C1(N)CCCC1>[CH:1]1([NH:6][C:7]2[N:12]3[N:13]=[C:14]([C:23]4[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=4)[C:15]([C:16]4[CH:21]=[CH:20][N:19]=[C:18]([NH:6][CH:1]5[CH2:5][CH2:4][CH2:3][CH2:2]5)[CH:17]=4)=[C:11]3[CH:10]=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 1

HCID 17953061HCID 17953061, compound

Product 1

HCID 10115190HCID 10115190, compoundYield 136.1%

Reagents, catalysts & solvents 1

HCID 2906CyclopentylamineSolvent

Procedure

A solution of N-cyclopentyl-2-(4-fluorophenyl)-3-(2-fluoro-4-pyridinyl)pyrazolo[1,5-α]pyridin-7-amine (37 mg, 0.10 mmol) in cyclopentylamine (4 mL) was heated to 150° C. in a sealed tube for 12 hours. Upon cooling to room temperature, the mixture was concentrated in vacuo and the residue was taken up in ether and washed with water and then brine. The aqueous layer was extracted with ether and the combined organics were dried over magnesium sulfate. Filtration and concentration followed by flash chromatography (4:1 to 2:1 hexanes:ethyl acetate) provided N-cyclopentyl-3-[2-(cyclopentylamino)-4-pyridinyl]-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-7-amine (31 mg, 72%) as a solid. 1H NMR (CDCl3): δ 8.01 (d, 1H), 7.64 (dd, 2H), 7.21 (t, 1H), 7.10–7.02 (m, 3H), 6.57 (d, 1H), 6.34 (s, 1H), 6.01 (d, 1H), 5.97 (d, 1H), 4.63 (broad, 1H), 4.02 (m, 1H), 3.79 (m, 1H), 2.16 (m, 2H), 1.96–1.42 (m, 14H); 19F NMR (CDCl3) δ −114.06; MS m/z 456 (M+1).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. washwashed with water
  3. extractionThe aqueous layer was extracted with ether
  4. dry with materialthe combined organics were dried over magnesium sulfate
  5. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-2d0aa13e3c0e4bdeb2e8db532fcd2632
Source dataset
uspto-grants-2007_01
Patent number
US07163940B2

Reaction notes

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