Hydrazine → HCID 178474120, compound

HRID 81025

Reaction equation

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

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of N-(3-(6-chloro-5-cyano-4-(4-phenoxyphenyl)pyridin-2-yl)phenyl)acetamide (25 mg, 0.057 mmol) and 35% aqueous hydrazine (0.051 mL, 0.568 mmol) in 2-propanol (1.5 mL) was heated to 160° C. under microwave for 1 h then cooled to room temperature. Purification with reverse phase HPLC (Sunfire S10 30×250 mm column), eluting with 60-90% solvent B (10% methanol-90% water-0.1% TFA) in solvent A (90% methanol-10% water-0.1% TFA), gave Example 25 as the faster eluting peak (18 mg, 41% yield, yellow solid) and Example 24 as the slower eluting peak (3 mg, 8% yield, yellow solid).

Workup

temperaturethen cooled to room temperature
customPurification with reverse phase HPLC (Sunfire S10 30×250 mm column)
washeluting with 60-90% solvent B (10% methanol-90% water-0.1% TFA) in solvent A (90% methanol-10% water-0.1% TFA)
customgave Example 25 as the
washfaster eluting peak (18 mg, 41% yield, yellow solid) and Example 24 as the
washslower eluting peak (3 mg, 8% yield, yellow solid)

Sources & evidence

ORD record: ord-bd940899d13e459c8c56ca64cf48df97
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846673B2

Linked notes

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