Ethyl Acetate → Tert-butyl 2-(4-(6-hydroxyquinolin-2-yl)benzoyl)hydrazinecarboxylate

HRID 1410580Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:20]=[CH:19][C:15]([C:16](O)=[O:17])=[CH:14][CH:13]=1)[CH:6]=[CH:5]2.CCN=C=NCCCN(C)C.[C:32]([NH:39][NH2:40])([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33].CCOC(C)=O>C(Cl)Cl.CN(C=O)C>[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:20]=[CH:19][C:15]([C:16]([NH:40][NH:39][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[O:17])=[CH:14][CH:13]=1)[CH:6]=[CH:5]2

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 4-(6-hydroxyquinolin-2-yl)benzoic acid (Compound 3, Example 3) (200 mg, 0.754 mmol), EDCI (145 mg, 0.754 mmol) and BocNHNH2 (100 mg, 0.754 mmol) in DCM (10 mL) and DMF (10 mL) was stirred at 25° C. overnight, followed by an aqueous/EtOAc workup. The crude was purified by column chromatography on silica gel (PE/EtOAc=1/1) to give the product (200 mg, yield 70%) as a yellow solid.

Workup

customThe crude was purified by column chromatography on silica gel (PE/EtOAc=1/1)

Sources & evidence

ORD record: ord-41d29df1a9ba44dcb4e0cf7c279dfc0c
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921562B2

Reaction notes

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