Hydrochloric Acid → HCID 66826234, compound

HRID 924893Notes

Reaction equation

HRID 924893 reaction equation
[CH3:1][N:2]1[C:6]([C:7](=O)[CH2:8][C:9]2[CH:13]=[CH:12][S:11][CH:10]=2)=[CH:5][CH:4]=[N:3]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>CCO>[CH2:15]([O:17][C:18]1[CH:19]=[C:20]([CH:21]2[C:8]([C:9]3[CH:13]=[CH:12][S:11][CH:10]=3)=[C:7]([C:6]3[N:2]([CH3:1])[N:3]=[CH:4][CH:5]=3)[NH:33][C:31](=[O:32])[NH:30]2)[CH:23]=[C:24]([N+:27]([O-:29])=[O:28])[C:25]=1[OH:26])[CH3:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 5848783-Ethoxy-4-hydroxy-5-nitrobenzaldehydeHCID 67061133HCID 67061133, compound2×

Product 1

HCID 66826234HCID 66826234, compoundYield 22.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 1-(1-methyl-1H-pyrazol-5-yl)-2-(thiophen-3-yl)ethanone (Intermediate 72) (90 mg, 0.32 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (110 mg, 0.52 mmol) and urea (52 mg, 0.87 mmol) in EtOH (4 mL) was added concentrated HCl (0.1 mL). The reaction was refluxed overnight. Purified by column chromatography and preparative HPLC to give Compound 139 as a yellow solid (32 mg, yield: 16.7%). 1HNMR (DMSO-d6 400 MHz): δ 10.44 (s, 1H), 8.91 (s, 1H), 7.75 (s, 1H), 7.57 (d, J=1.6 Hz, 1H), 7.53 (d, J=2.0 Hz, 1H), 7.34-7.36 (m, 2H), 7.06-7.07 (m, 1H), 6.39 (d, J=2.0 Hz, 1H), 6.21 (d, J=4.8 Hz, 1H), 5.42 (d, J=2.4 Hz, 3H), 4.14 (q, J=7.2 Hz, 2H), 3.62 (s, 3H), 1.42 (t, J=7.2 Hz, 3H); MS (ESI): m/z 442.0 [M+1]+.

Workup

  1. temperatureThe reaction was refluxed overnight
  2. customPurified by column chromatography and preparative HPLC

Sources & evidence

ORD record
ord-8ec0b94e3bdc4206bd7698171b8334d3
Source dataset
uspto-grants-2016_03
Patent number
US09283229B2

Reaction notes

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