Hydrazine hydrate (1:1) → HCID 44600314, compound

HRID 446785Notes

Reaction equation

HRID 446785 reaction equation
O=[C:2]([C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1)[CH:3]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=2)=[CH:10][CH:9]=1)[C:4]([O:6]C)=O.[NH2:32][NH2:33].O>C(O)C>[N:29]1[CH:30]=[CH:31][C:26]([C:2]2[NH:33][NH:32][C:4](=[O:6])[C:3]=2[C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]3[CH:25]=[CH:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[N:17]=3)=[CH:10][CH:9]=2)=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 58368007HCID 58368007, compound

Product 1

HCID 44600314HCID 44600314, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of methyl 3-oxo-3-(pyridin-4-yl)-2-(4-(quinolin-2-ylmethoxy)phenyl)propanoate (0.2 g, 0.48 mmol) in ethanol (5 mL), NH2NH2.H2O (0.12 g, 2.42 mmol) and TEA (0.146 g, 1.45 mmol) were added dropwise at RT. The reaction mixture was then refluxed for 16 h and then concentrated in vacuo to obtain crude product. The crude material was washed with water (5 mL) and ether (5 mL) to afford 5-(pyridin-4-yl)-4-(4-(quinolin-2-ylmethoxy)phenyl)-1H-pyrazol-3(2H)-one (70 mg, 37%) as a white solid. 1H NMR (500 MHz, d6-DMSO): δ 9.12 (bs, 1H), 8.38 (d, J=7.2 Hz, 2H), 8.02-7.96 (m, 3H), 7.76 (t, J=7.6 Hz, 2H), 7.64-7.56 (m, 3H), 7.16 (d, J=7.2 Hz, 2H), 6.96 (d, J=7.2 Hz, 2H), 5.38 (s, 2H), 3.21 (s, 1H). MS: M+H: m/z=395.1 and HPLC: 80%, (Condition-C).

Workup

  1. temperatureThe reaction mixture was then refluxed for 16 h
  2. concentrationconcentrated in vacuo
  3. customto obtain crude product
  4. washThe crude material was washed with water (5 mL) and ether (5 mL)

Sources & evidence

ORD record
ord-fcc1245363594ba884bf4f6982037a52
Source dataset
uspto-grants-2013_07
Patent number
US08481534B2

Reaction notes

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