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

HRID 2201434Notes

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 IV-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-071909f6ad044c22a957ff0c62def8a5
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09364481B2

Reaction notes

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