Hydrochloric Acid → HCID 56961403, compound

HRID 401041Notes

Reaction equation

HRID 401041 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([F:13])[C:11]=1[OH:12])[CH:7]=O)[CH3:2].[C:14]1([C:20](=O)[CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[NH2:29][C:30]([NH2:32])=[O:31].Cl>C(O)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:7]2[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:20]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[NH:32][C:30](=[O:31])[NH:29]2)[CH:9]=[C:10]([F:13])[C:11]=1[OH:12])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 99482-PhenylacetophenoneHCID 86669331HCID 86669331, compound2×

Product 1

HCID 56961403HCID 56961403, compoundYield 10.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 3-ethoxy-5-fluoro-4-hydroxybenzaldehyde (Intermediate 32) (160 mg, 0.87 mmol), 1,2-diphenyl-ethanone (170 mg, 0.87 mmol), urea (157 mg, 2.61 mmol), and concentrated HCl solution (0.2 mL) in ethanol (20 mL) was degassed and refluxed for 3 days under N2 protection. The solvent was removed under reduced pressure, and the residue was purified by preparative HPLC to give Compound 64 (30 mg, 10.6%). 1H NMR (DMSO-d6 300 MHz) δ 9.08 (s, br, 1H), 8.63 (s, 1H), 7.42 (s, 1H), 7.19-7.26 (m, 5H), 7.01-7.03 (m, 3H), 6.72-6.81 (m, 4H), 5.04 (d, J=2.7 Hz, 1H), 3.99 (q, J1=6.9 Hz, J2=9.0 Hz, 2H), 1.33 (t, J=6.9 Hz, 3H); MS (ESI): m/z 405.1 [M+1]+.

Workup

  1. customwas degassed
  2. temperaturerefluxed for 3 days under N2 protection
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-137f0ce252c946d3bd83cacf9b9968e9
Source dataset
uspto-grants-2014_06
Patent number
US08741915B2

Reaction notes

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