Hydrazine → N-(4-(3-Amino-4-(4-phenoxyphenyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)phenyl)acetamide

HRID 81067Notes

Reaction equation

Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:12][CH:11]=2)[N:5]=[C:4]([C:23]2[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:32])[CH3:31])=[CH:25][CH:24]=2)[CH:3]=1.[NH2:33][NH2:34]>CN(C)C=O>[NH2:9][C:8]1[C:7]2[C:6]([C:10]3[CH:15]=[CH:14][C:13]([O:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[CH:12][CH:11]=3)=[N:5][C:4]([C:23]3[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:32])[CH3:31])=[CH:25][CH:24]=3)=[CH:3][C:2]=2[NH:34][N:33]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of N-(4-(4-chloro-5-cyano-6-(4-phenoxyphenyl)pyridin-2-yl)phenyl)acetamide (24.9 mg, 0.057 mmol), 35% aqueous hydrazine (20 μL, 0.637 mmol) and N,N-dimethylformamide (0.5 mL) in a sealed tube was heated to 100° C. for 3 h, 120° C. for 6 h and concentrated. Silica gel chromatography, eluting with 0-10% methanol in dichloromethane, gave the desired product. The material was triturated with dichloromethane and filtered to give Example 200 as light yellow solid (9.4 mg, 38% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.20 (1H, s), 10.08 (1H, s), 8.11 (2H, δ, J=8.78 Hz), 7.81-7.84 (2H, m), 7.69 (2H, δ, J=8.78 Hz), 7.63 (1H, s), 7.43-7.48 (2H, m), 7.13-7.23 (5H, m), 4.83 (2H, s), 2.07 (3H, s); MS (ES+) m/z: 436 (M+H); LC retention time: 3.200 min (analytical HPLC Method A).

Workup

concentrationconcentrated
washSilica gel chromatography, eluting with 0-10% methanol in dichloromethane

Sources & evidence

ORD record: ord-6228169742f140408406c84c74db0ef4
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846673B2

Reaction notes

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