Hydrochloric Acid → HCID 58964472, compound

HRID 2069307Notes

Reaction equation

HRID 2069307 reaction equation
[C:1]1([S:7]([NH:10][N:11]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][C:16]([C:30]([F:33])([F:32])[F:31])=[C:17]([N:22]4[CH:26]=[C:25]([C:27]([OH:29])=[O:28])[N:24]=[CH:23]4)[CH:18]=3)[NH:13][C:12]2=[O:34])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH3:36]O>>[CH3:36][O:28][C:27]([C:25]1[N:24]=[CH:23][N:22]([C:17]2[CH:18]=[C:19]3[C:14](=[CH:15][C:16]=2[C:30]([F:33])([F:32])[F:31])[NH:13][C:12](=[O:34])[N:11]([NH:10][S:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)(=[O:8])=[O:9])[C:20]3=[O:21])[CH:26]=1)=[O:29]

Participants

4

Reactant 3

HCID 313Hydrochloric Acid2×HCID 887Methanol2×HCID 11605658HCID 11605658, compound

Product 1

HCID 58964472HCID 58964472, compound

Procedure

A solution of 20 mg (0.04 mmol) of 1-(3-benzenesulfonylamino-2,4-dioxo-7-trifluoromethyl-1,2,3,4-tetrahydro-quinazolin-6-yl)-1H-imidazole-4-carboxylic acid in 50 ml of a 6 M solution of hydrochloric acid in methanol is stirred at 70° C. for two days. Every half day another 50 ml of a 6 M solution of hydrochloric acid in methanol is added. Subsequently the solvent and hydrochloric acid are evaporated to yield 1-(3-benzenesulfonylamino-2,4-dioxo-7-trifluoromethyl-1,2,3,4-tetrahydro-quinazolin-6-yl)-1H-imidazole-4-carboxylic acid methyl ester: 1H-NMR; DMSO-d6 (400 MHz, ppm): 8.16 (s, 1H, imidazole); 8.10 (s, 1H, aromatic); 7.98 (s, 1H, imidazole); 7.70 (s, 1H, aromatic); 3.79 (s, 3H, COOCH3). LC-MS: 510 [M+H]+; Agilent LC/MSD 1100 Series, LC-MS method: Column: SunFireC8, 4.6*50 mm, 3.5 μm; positive MS; water/acetonitril 95:5 to 5:95 in 5 min, flow: 1.5 ml/min.

Workup

  1. customSubsequently the solvent and hydrochloric acid are evaporated

Sources & evidence

ORD record
ord-ab25af518fa647ea86a17c8ac7359cdb
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

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