Hydrochloric Acid → HCID 51349083, compound

HRID 401089Notes

Reaction equation

HRID 401089 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9](=O)[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.[CH2:18]([O:20][C:21]1[CH:22]=[C:23]([CH:26]=[C:27]([N+:30]([O-:32])=[O:31])[C:28]=1[OH:29])[CH:24]=O)[CH3:19].[NH2:33][C:34]([NH2:36])=[O:35].Cl>CCO.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:36][C:34](=[O:35])[NH:33][CH:24]([C:23]3[CH:26]=[C:27]([N+:30]([O-:32])=[O:31])[C:28]([OH:29])=[C:21]([O:20][CH2:18][CH3:19])[CH:22]=3)[C:10]=2[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 5848783-Ethoxy-4-hydroxy-5-nitrobenzaldehydeHCID 27575661-(3-Chloro-5-fluorophenyl)-2-phenylethanone2×

Product 1

HCID 51349083HCID 51349083, compoundYield 58.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-(3-chloro-5-fluorophenyl)-2-phenylethanone (Intermediate 60) (150 mg, 0.60 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (116 mg, 0.55 mmol), urea (99 mg, 1.65 mmol), concentrated HCl (0.05 mL, 0.55 mmol) in EtOH (5 mL) was refluxed overnight. Followed standard aqueous/EtOAc workup and purified by preparative HPLC to give Compound 121 (155 mg, yield 58%). 1H NMR (DMSO-d6 400 MHz): δ 10.27 (brs, 1H), 8.85 (s, 1H), 7.58 (s, 1H), 7.40 (d, J=1.6 Hz, 1H), 7.34 (d, J=8.8 Hz, 1H), 7.25 (s, 1H), 7.12 (d, J=6.4 Hz, 2H), 7.08 (d, J=7.6 Hz, 2H), 7.01 (d, J=7.2 Hz, 1H), 6.88 (d, J=7.2 Hz, 2H), 5.27 (d, J=2.4 Hz, 1H), 4.09-3.99 (m, 2H), 1.32 (t, J=7.2 Hz, 3H); MS (ESI): m/z 484.1 [M+1]+.

Workup

  1. temperaturewas refluxed overnight
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-25badd60da31427389cc87a133680b13
Source dataset
uspto-grants-2014_06
Patent number
US08741915B2

Reaction notes

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