Hydrazine → 5-(2-(2-(4-fluorophenyl)-2-methylpropylamino)pyrimidin-5-yl)-1H-indazol-3-amine

HRID 1474091Notes

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

To a 5 mL microwave reaction vessel was added 2-fluoro-5-(2-(2-(4-fluorophenyl)-2-methylpropylamino)pyrimidin-5-yl)benzonitrile (220 mg, 0.6 mmol), hydrazine (500 μL), and propanol (5 mL). The reaction was heated to 120° C. and stirred for 3 h. The reaction was concentrated and purified by reverse phase column chromatography to give 95 mg (42%) of 5-(2-(2-(4-fluorophenyl)-2-methylpropylamino)pyrimidin-5-yl)-1H-indazol-3-amine as a white solid (m/z [M+H]=377.1).

Workup

concentrationThe reaction was concentrated
custompurified by reverse phase column chromatography

Sources & evidence

ORD record: ord-72a4a43500af44ca9ecc123882b0901e
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018223B2

Reaction notes

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