Hydrochloric Acid → HCID 56961614, compound

HRID 2177918Notes

Reaction equation

HRID 2177918 reaction equation
[C:1]1([CH2:7][C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:16]([O:18][C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([N+:28]([O-:30])=[O:29])[C:26]=1[OH:27])[CH:22]=O)[CH3:17].[NH2:31][C:32]([NH2:34])=[O:33].Cl>C(O)C>[CH2:16]([O:18][C:19]1[CH:20]=[C:21]([CH:22]2[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=3)[NH:34][C:32](=[O:33])[NH:31]2)[CH:24]=[C:25]([N+:28]([O-:30])=[O:29])[C:26]=1[OH:27])[CH3:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 2560732-phenyl-1-(pyridin-2-yl)ethanone2×HCID 5848783-Ethoxy-4-hydroxy-5-nitrobenzaldehyde

Product 1

HCID 56961614HCID 56961614, compoundYield 30.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-phenyl-1-(pyridin-2-yl)ethanone (Intermediate 27) (200 mg, 1.01 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (214.1 mg, 1.01 mmol), urea (182.5 mg, 3.04 mmol), and concentrated hydrochloric acid solution (0.3 mL) in ethanol (1 mL) was refluxed for 60 h. After being cooled down to room temperature, the mixture was evaporated, and purified by preparative HPLC to give Compound 59 (132.5 mg, yield 30.2%). 1H NMR (DMSO-d6 400 MHz): δ10.26 (brs, 1H), 8.59 (d, J=4.4 Hz, 1H), 8.37 (s, 1H), 7.62-7.54 (m, 2H), 7.42 (s, 1H), 7.30-7.27 (m, 1H), 7.14 (d, J=6.4 Hz, 4H), 6.93-6.90 (m, 3H), 5.25 (s, 1H), 4.03-3.99 (m, 2H), 1.33-1.29 (m, 3H); MS (ESI): m/z 433.0 [M+H]+.

Workup

  1. temperaturewas refluxed for 60 h
  2. customthe mixture was evaporated
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-6332a1f1bb814673b8e1f19ec5f5f69d
Source dataset
uspto-grants-2015_06
Patent number
US09067893B2

Reaction notes

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