Isopropanol → HCID 59139877, compound

HRID 1624901Notes

Reaction equation

[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]([C:14]([OH:16])=[O:15])=[N:10][N:9]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([NH:23][C:24](=[O:26])[CH3:25])[CH:18]=3)[C:8]2=[O:27])=[CH:4][CH:3]=1.[CH:30](O)([CH3:32])[CH3:31]>S(=O)(=O)(O)O.C([O-])(O)=O.[Na+]>[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]([C:14]([O:16][CH:30]([CH3:32])[CH3:31])=[O:15])=[N:10][N:9]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([NH:23][C:24](=[O:26])[CH3:25])[CH:18]=3)[C:8]2=[O:27])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

According to Scheme 7 Step 5: A mixture of 4-(4-chlorobenzyl)-2-(3-acetamidophenyl)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid 7.6 (100 mg, 0.24 mmol), isopropylalcohol (3 mL) and sulfuric acid (2 drops) was heated at 80° C. for 20 hours. The reaction mixture was diluted with a saturated solution of NaHCO3 (50 mL) and the aqueous layer was extracted twice with DCM (50 mL). The organic layers were combined and selectively dried over MgSO4, filtered and concentrated under reduced pressure to afford a brown solid. The crude solid was purified by flash chromatography with silica gel (Merck Flashmart prepacked column 7 g SiO2) using CH2Cl2/MeOH 98/2 as eluant to afford isopropyl 4-(4-chlorobenzyl)-2-(3-acetamidophenyl)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylate (33 mg, 30%) as a beige solid.

Workup

extractionthe aqueous layer was extracted twice with DCM (50 mL)
dry with materialselectively dried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customto afford a brown solid
customThe crude solid was purified by flash chromatography with silica gel (Merck Flashmart prepacked column 7 g SiO2)

Sources & evidence

ORD record: ord-00798d087f074640a3aa1e990dbcbe9d
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08779129B2

Reaction notes

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