Ethyl Acetate → HCID 136078985, compound

HRID 1472658Notes

Reaction equation

HRID 1472658 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:21]=[CH:20][C:15]([C:16]([NH:18][NH2:19])=[O:17])=[CH:14][CH:13]=1)[CH:6]=[CH:5]2.C1N=CN([C:27](N2C=NC=C2)=[O:28])C=1.CCOC(C)=O>C(Cl)Cl>[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:13]=[CH:14][C:15]([C:16]3[O:17][C:27](=[O:28])[NH:19][N:18]=3)=[CH:20][CH:21]=1)[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 682631,1'-CarbonyldiimidazoleHCID 669800744-(6-Hydroxyquinolin-2-yl)benzohydrazide

Product 1

HCID 136078985HCID 136078985, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(6-hydroxyquinolin-2-yl)benzohydrazide (90 mg, 0.322 mmol) and CDI (454 mg, 3.22 mmol) in DCM (20 mL) was refluxed overnight. The resulting mixture was cooled to room temperature, followed by an aqueous/EtOAc workup. The crude was purified by prep-HPLC (0.1% TFA as additive) to give Compound IV-24 (18 mg, yield 11%). 1H NMR (CD3OD, 400 MHz): δ 8.64-8.48 (m, 1H), 8.38-7.96 (m, 6H), 7.66-7.24 (m, 2H). MS (ESI): m/z 305.7 [M+H]+.

Workup

  1. temperaturewas refluxed overnight
  2. customThe crude was purified by prep-HPLC (0.1% TFA as additive)
  3. customto give Compound IV-24 (18 mg, yield 11%)

Sources & evidence

ORD record
ord-73b611156add476e804ef84d120a5229
Source dataset
uspto-grants-2015_04
Patent number
US09012646B2

Reaction notes

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