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

HRID 2280456Notes

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-c22f7af5d1b24560b9df2d5c8a7f89e9
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09139528B2

Reaction notes

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