Cyclopentylamine → HCID 10069758, compound

HRID 859967Notes

Reaction equation

Cl[C:2]1[N:7]2[N:8]=[C:9]([CH2:18][CH2:19][CH3:20])[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[C:13](F)[CH:12]=3)=[C:6]2[CH:5]=[CH:4][CH:3]=1.[CH:21]1([NH2:26])[CH2:25][CH2:24][CH2:23][CH2:22]1>>[CH:21]1([NH:26][C:2]2[N:7]3[N:8]=[C:9]([CH2:18][CH2:19][CH3:20])[C:10]([C:11]4[CH:16]=[CH:15][N:14]=[C:13]([NH:26][CH:21]5[CH2:25][CH2:24][CH2:23][CH2:22]5)[CH:12]=4)=[C:6]3[CH:5]=[CH:4][CH:3]=2)[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

Reactant 2

HCID 2906Cyclopentylamine

HCID 10334377HCID 10334377, compound

Product 1

HCID 10069758HCID 10069758, compoundYield 77%

Procedure

A solution of 7-chloro-3-(2-fluoropyridin-4-yl)-2-propylpyrazolo[1,5-a]pyridine (41 mg, 0.14 mmol) in cyclopentylamine (5 mL) was heated in a sealed vessel at 150° C. for 18 h. The mixture was cooled to room temperature and concentrated in vacuo and the residue was purified by flash chromatography on silica gel (2:1 hexane-ethyl acetate) to give N-cyclopentyl-3-[2-(cyclopentylamino)pyridin-4-yl]-2-propylpyrazolo[1,5-a]pyridin-7-amine (44 mg, 77%) as a yellow solid. 1H NMR (CDCl3) δ 8.10 (d, 1H), 7.18 (t, 1H), 7.00 (d, 1H), 6.73 (d, 1H), 6.52 (s, 1H), 5.97–5.91 (m, 2H), 5.07 (m, 1H), 4.00 (m, 2H), 2.95 (t, 2H), 2.18–2.05 (m, 4H), 1.87–1.57 (m, 14H), 1.02 (t, 3H); MS m/z 404 (M+1).

Workup

concentrationconcentrated in vacuo
customthe residue was purified by flash chromatography on silica gel (2:1 hexane-ethyl acetate)

Sources & evidence

ORD record: ord-366540fa6f054b08aa1f9dcdcec0816b
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07153863B2

Reaction notes

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