Hydrazine → N-cyclopentyl-4-[2-(4-fluorophenyl)-7-hydrazinopyrazolo[1,5-a]pyridin-3-yl]-6-methyl-2-pyrimidinamine

HRID 1373795Notes

Reaction equation

Cl[C:2]1[N:7]2[N:8]=[C:9]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[C:10]([C:11]3[CH:16]=[C:15]([CH3:17])[N:14]=[C:13]([NH:18][CH:19]4[CH2:23][CH2:22][CH2:21][CH2:20]4)[N:12]=3)=[C:6]2[CH:5]=[CH:4][CH:3]=1.[NH2:31][NH2:32]>C(O)C.C(OCC)(=O)C>[CH:19]1([NH:18][C:13]2[N:12]=[C:11]([C:10]3[C:9]([C:24]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=4)=[N:8][N:7]4[C:2]([NH:31][NH2:32])=[CH:3][CH:4]=[CH:5][C:6]=34)[CH:16]=[C:15]([CH3:17])[N:14]=2)[CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 4-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-N-cyclopentyl-6-methyl-2-pyrimidinamine (100 mg, 0.237 mmol) in ethanol (1 mL) was added hydrazine (500 uL, 15.9 mmol). The reaction mixture was heated in a sealed tube at 90° C. for 72 hours. The mixture was cooled and diluted with ethyl acetate and washed with saturated aqueous sodium bicarbonate, water and brine. The combined organics were dried over magnesium sulfate. Filtration and concentration followed by flash chromatography (38:2 dichloromethane-methanol) provided N-cyclopentyl-4-[2-(4-fluorophenyl)-7-hydrazinopyrazolo[1,5-α]pyridin-3-yl]-6-methyl-2-pyrimidinamine (45 mg, 46%) as a yellow solid. Rf 0.43 (38:2 CH2Cl2-MeOH); 1H NMR (CDCl3) δ 7.78 (1H), 7.62 (2H), 7.35 (1H), 7.20 (1H), 7.12 (2H), 6.45 (1H), 6.24 (1H), 5.03 (1H), 4.35 (1H), 3.85 (2H), 2.18 (3H), 2.02 (2H), 1.62 (6H); MS m/z 418 (M+1).

Workup

temperatureThe mixture was cooled
washwashed with saturated aqueous sodium bicarbonate, water and brine
dry with materialThe combined organics were dried over magnesium sulfate
filtrationFiltration and concentration

Sources & evidence

ORD record: ord-3973ba1c19b24b729ead74990c190b1c
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07163940B2

Reaction notes

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