HCID 18789810, compound → HCID 53855206, compound

HRID 1106702Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([Cl:13])[CH:12]=1)[O:5][CH2:6][C:7](=O)[CH3:8].Cl.[NH2:15][O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N:24]1[C:28]([O:29][CH3:30])=[N:27][N:26]([CH3:31])[C:25]1=[O:32]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([Cl:13])[CH:12]=1)[O:5][CH2:6][C:7](=[N:15][O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N:24]1[C:28]([O:29][CH3:30])=[N:27][N:26]([CH3:31])[C:25]1=[O:32])[CH3:8]

Participants

Conditions

Temperature: 90 °C

Procedure

To a stirred solution of the title compound of Step A (0.33 g, 1.5 mmol) in pyridine (30 mL) under a nitrogen atmosphere was added the title compound of Step C (0.43 g, 1.5 mmol) and the resulting mixture was heated at 90 ° C. for 2 h. The reaction mixture was allowed to cool to room temperature overnight. The reaction mixture was concentrated under reduced pressure and the residue was diluted with 1 N aqueous HCl and was extracted three times with ethyl acetate. After drying (MgSO4), the combined organic extracts were concentrated under reduced pressure. Chromatography of the residue on silica gel (200 g) with 1:1 hexane: ethyl acetate afforded 0.14 g of the title compound of Step D, a compound of the invention, as an oil. 300 MHz 1H NMR CDCl3): δ 7.44 (m,3H), 7.23 (m,1H), 6.96 (m,1H), 6.81 (m,2H), 5.12 (q,2H), 4.44 (s,2H), 3.9 (s,3H), 3.43 (s,3H), 1.89 (s,3H).

Workup

temperatureto cool to room temperature overnight
concentrationThe reaction mixture was concentrated under reduced pressure
additionthe residue was diluted with 1 N aqueous HCl
extractionwas extracted three times with ethyl acetate
dry with materialAfter drying (MgSO4)
concentrationthe combined organic extracts were concentrated under reduced pressure

Sources & evidence

ORD record: ord-3ddc0e6281384214b3c4e04b8c90f687
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06057352

Reaction notes

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