Hydrochloric Acid → HCID 51347186, compound

HRID 401125Notes

Reaction equation

HRID 401125 reaction equation
[CH3:1][N:2]([CH3:18])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[C:13]=1[OH:14])[CH:9]=O.[C:19]1([C:25](=O)[CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[NH2:34][C:35]([NH2:37])=[O:36].Cl>C(O)C>[CH3:1][N:2]([CH3:18])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:9]2[C:26]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[C:25]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[NH:37][C:35](=[O:36])[NH:34]2)[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[C:13]=1[OH:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 99482-PhenylacetophenoneHCID 86669347HCID 86669347, compound2×

Product 1

HCID 51347186HCID 51347186, compoundYield 24.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-(2-(dimethylamino)ethoxy)-4-hydroxy-5-nitrobenzaldehyde (Intermediate 89) (100 mg, 0.39 mmol), 1,2-diphenyl-ethanone (77 mg, 0.39 mmol) and urea (70 mg, 1.2 mmol) in ethanol (3 mL) was added conc. HCl (0.2 mL); the resulting mixture was refluxed overnight. The mixture was concentrated and purified by prep-HPLC (0.1% TFA as additive) to give Compound 170 (45 mg, yield 22%) as yellow solid. 1H NMR (MeOD 400 MHz) δ 7.81 (d, J=2.0 Hz, 1H), 7.39 (d, J=2.0 Hz, 1H), 7.38-7.25 (m, 5H), 7.16-7.04 (m, 3H), 6.98-6.88 (m, 2H), 5.47 (s, 1H), 4.46-4.35 (m, 2H), 3.71-3.62 (m, 2H), 3.08 (s, 6H). MS (ESI): m/z 475.1 [M+1]+.

Workup

  1. temperaturethe resulting mixture was refluxed overnight
  2. concentrationThe mixture was concentrated
  3. custompurified by prep-HPLC (0.1% TFA as additive)

Sources & evidence

ORD record
ord-2bb4c9778d1545f9af8c8c32d89dad30
Source dataset
uspto-grants-2014_06
Patent number
US08741915B2

Reaction notes

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