2-(2-Aminoethyl)-1-methylpyrrolidine → N-[2-(4-fluorophenyl)-3-(4-pyridinyl)pyrazolo[1,5-alpha]pyridin-7-yl]-N-[2-(1-methyl-2-pyrrolidinyl)ethyl]amine

HRID 1373830Notes

Reaction equation

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

Participants

Conditions

Temperature: 85 °C

Procedure

To a stirred solution of 7-chloro-2-(4-fluorophenyl)-3-(4-pyridinyl)pyrazolo[1,5-α]pyridine (50 mg, 0.154 mmol) in 1 mL of isopropanol was added excess of 2-(1-methylpyrrolidin-2-yl)ethanamine (1 mL). The mixture was heated to reflux at 85° C. overnight. The mixture was evaporated to dryness and purified by preparative thin layer chromatography to give N-[2-(4-fluorophenyl)-3-(4-pyridinyl)pyrazolo[1,5-α]pyridin-7-yl]-N-[2-(1-methyl-2-pyrrolidinyl)ethyl]amine as peach solid in 17% yield (28.3% yield based on recovered starting material). 1H NMR (CDCl3): δ 8.58 (dd, 2H, J=1.4, 4.6 Hz), 7.59–7.62 (m, 2H), 7.25–7.32 (m, 3H), 7.04–7.14 (m, 3H), 6.83 (t, 1H, J=5.3 Hz), 5.98 (d, 1H, J=7.4 Hz), 3.40–3.55 (m, 2H), 3.13–3.19 (m, 1H), 2.43 (s, 3H), 2.36–2.43 (m, 1H), 2.20–2.29 (m, 1H), 1.66–2.20 (m, 6H); MS (ES+ve): 418 (10, M+3), 417 (20, M+2), 416 (60, M+1), 112 (100).

Workup

temperatureThe mixture was heated
customThe mixture was evaporated to dryness
custompurified by preparative thin layer chromatography

Sources & evidence

ORD record: ord-02f87673059944cdbdc5d86819f7f4cc
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07163940B2

Reaction notes

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