Hydrochloric Acid → HCID 51347189, compound

HRID 2178013Notes

Reaction equation

HRID 2178013 reaction equation
[CH:1]1([C:7](=O)[CH2:8][C:9]2[CH:13]=[CH:12][S:11][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:15]([O:17][C:18]1[CH:19]=[C:20]([CH:23]=[C:24]([N+:27]([O-:29])=[O:28])[C:25]=1[OH:26])[CH:21]=O)[CH3:16].[NH2:30][C:31]([NH2:33])=[O:32].Cl>C(O)C>[CH:1]1([C:7]2[NH:33][C:31](=[O:32])[NH:30][CH:21]([C:20]3[CH:23]=[C:24]([N+:27]([O-:29])=[O:28])[C:25]([OH:26])=[C:18]([O:17][CH2:15][CH3:16])[CH:19]=3)[C:8]=2[C:9]2[CH:13]=[CH:12][S:11][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 5848783-Ethoxy-4-hydroxy-5-nitrobenzaldehydeHCID 61054664HCID 61054664, compound2×

Product 1

HCID 51347189HCID 51347189, compoundYield 9.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-cyclohexyl-2-(thiophen-3-yl)ethanone (Intermediate 95) (176 mg, 0.56 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (140 mg, 0.67 mmol), urea (100 mg, 1.68 mmol) and concentrated HCl solution (0.1 mL) in absolute ethanol (5 mL) was reflux under N2 overnight. Solvent was removed, and residue was purified by column chromatography and prep-HPLC to give Compound 174 (23 mg, yield: 9%) as a yellow solid. 1H NMR (DMSO-d6400 MHz): δ 10.25 (brs, 1H), 8.26 (s, 1H), 7.45 (dd, J=4.8, 2.0 Hz, 1H), 7.35-7.25 (m, 2H), 7.09 (d, J=1.6 Hz, 1H), 7.06 (d, J=1.6 Hz, 1H), 6.85 (d, J=4.0 Hz, 1H), 4.98 (d, J=2.4 Hz, 1H), 4.10-3.90 (m, 2H), 1.90-1.40 (m, 7H), 1.35 (t, J=7.2 Hz, 3H), 1.20-1.00 (m, 3H). MS (ESI): m/z 444.2 [M+1]+.

Workup

  1. temperaturewas reflux under N2 overnight
  2. customSolvent was removed
  3. customresidue was purified by column chromatography

Sources & evidence

ORD record
ord-a7c0b66e6afd4e938e74afe52124e6cf
Source dataset
uspto-grants-2015_06
Patent number
US09067893B2

Reaction notes

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