4-Formylbenzoic acid → HCID 87956700, compound

HRID 897254Notes

Reaction equation

HRID 897254 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[O:10][C:9](=[O:14])[CH:8]=[C:7]2[NH:15][CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.[CH:22]([C:24]1[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=1)=O>>[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[O:10][C:9](=[O:14])[CH:8]=[C:7]2[NH:15][CH:16]1[CH2:21][CH2:20][N:19]([CH2:22][C:24]2[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=2)[CH2:18][CH2:17]1

Participants

3

Reactant 2

HCID 120884-Formylbenzoic acidHCID 22348292HCID 22348292, compound

Product 1

HCID 87956700HCID 87956700, compound

Procedure

According to Procedure C above, (I) (0.300 g of hydrochloride salt; 1.09 mmol) and 4-formyl-benzoic acid were allowed to react to afford after HPLC purification and precipitation with hydrochloric acid as described before, 0.182 g (35.4%) of the title compound. MS (DCI/NH3)(+)Q1MS m/z 409 (M+H)+; 1H NMR (500 MHz, pyridine-d5) δ ppm 1.78 (m, 2H), 2.13 (m, 4H), 2.89 (m, 2H), 3.42 (s, 3H), 3.56 (m, 1H), 3.57 (s, 2H), 5.72 (s, 1H), 7.15 (dd, J=9.05, 2.81 Hz, 1H), 7.34 (d, J=9.05 Hz, 1H), 7.53 (d, J=8.11 Hz, 2H), 7.62 (br d, J=7.18 Hz, N H), 7.70 (d, J=2.50 Hz, 1H) 8.41 (d, J=8.11 Hz, 2H).

Workup

  1. customto react
  2. customto afford
  3. customafter HPLC purification and precipitation with hydrochloric acid

Sources & evidence

ORD record
ord-f0f0aa7544f042108d0b46b1c8e49dff
Source dataset
uspto-grants-2005_07
Patent number
US06921821B2

Reaction notes

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