Cyclopentylamine → HCID 10018928, compound

HRID 859965Notes

Reaction equation

F[C:2]1[CH:7]=[C:6]([C:8]2[C:9]([CH2:17][CH2:18][CH3:19])=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=23)[CH:5]=[CH:4][N:3]=1.[CH:20]1([NH2:25])[CH2:24][CH2:23][CH2:22][CH2:21]1>>[CH:20]1([NH:25][C:2]2[CH:7]=[C:6]([C:8]3[C:9]([CH2:17][CH2:18][CH3:19])=[N:10][N:11]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=34)[CH:5]=[CH:4][N:3]=2)[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

Reactant 2

HCID 2906Cyclopentylamine

HCID 100609173-(2-fluoropyridin-4-yl)-2-propylpyrazolo[1,5-a]pyridine

Product 1

HCID 10018928HCID 10018928, compoundYield 98%

Procedure

A solution of 3-(2-fluoropyridin-4-yl)-2-propylpyrazolo[1,5-a]pyridine (126 mg, 0.49 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-4-(2-propylpyrazolo[1,5-a]pyridin-3-yl)pyridin-2-amine (155 mg, 98%) as a yellow solid. 1H NMR (CDCl3) δ 8.41 (d, 1H), 8.07 (d, 1H), 7.58 (d, 1H), 7.14 (t, 1H), 6.74 (td, 1H), 6.66 (dd, 1H), 6.45 (s, 1H), 5.01 (broad, 1H), 3.95 (m, 1H), 2.91 (t, 2H), 2.04 (m, 2H), 1.80–1.50 (m, 8H), 0.98 (t, 3H); MS m/z 321 (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-7729b3589d87463a9e61e2ba48f97229
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07153863B2

Reaction notes

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