Ethyl Acetate → HCID 136078936, compound

HRID 1627638Notes

Reaction equation

HRID 1627638 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([C:13]1[CH:18]=[CH:17][C:16]([C:19]([NH:21][NH:22][C:23]([O:25]C(C)(C)C)=O)=[S:20])=[CH:15][CH:14]=1)[CH:7]=[CH:6]2.[Al+3].[Cl-].[Cl-].[Cl-].CCOC(C)=O>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([C:13]1[CH:18]=[CH:17][C:16]([C:19]3[S:20][C:23](=[O:25])[NH:22][N:21]=3)=[CH:15][CH:14]=1)[CH:7]=[CH:6]2

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 6451240Aluminum(III) ChlorideHCID 86698072HCID 86698072, compound

Product 1

HCID 136078936HCID 136078936, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl 2-(4-(6-methoxyquinolin-2-yl)phenylcarbonothioyl)hydrazinecarboxylate (500 mg, 1.49 mmol) and AlCl3 (600 mg, 4.50 mmol) in anhydrous DCM (50 mL) was refluxed overnight. Reaction was cooled, followed by an aqueous/EtOAc workup. The residue was purified by prep-HPLC (0.1% TFA as additive) to give Compound IV-33 (35 mg, yield 7%) as a solid. 1H NMR (DMSO-d6, 400 MHz): δ 13.22 (brs, 1H), 10.22 (brs, 1H), 8.40-8.28 (m, 3H), 8.11 (d, J=8.8 Hz, 1H), 7.98 (d, J=8.8 Hz, 1H), 7.86 (d, J=8.4 Hz, 2H), 7.38 (dd, J=9.2, 2.8 Hz, 1H), 7.22 (d, J=2.8 Hz, 1H). MS (ESI): m/z 321.7 [M+H]+.

Workup

  1. temperaturewas refluxed overnight
  2. customReaction
  3. temperaturewas cooled
  4. customThe residue was purified by prep-HPLC (0.1% TFA as additive)
  5. customto give Compound IV-33 (35 mg, yield 7%) as a solid

Sources & evidence

ORD record
ord-2f4aa8f3cc1543c4883130cc04182345
Source dataset
uspto-grants-2014_07
Patent number
US08785643B2

Reaction notes

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