N-Methylformamide → HCID 54759161, compound

HRID 2069292Notes

Reaction equation

HRID 2069292 reaction equation
CO[C:3]([C:5]1[N:6]=[CH:7][N:8]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][C:19]=2[C:20]([F:23])([F:22])[F:21])[NH:16][C:15](=[O:24])[N:14]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])[C:13]3=[O:30])[CH:9]=1)=[O:4].[CH3:31][NH:32]C=O.C[O-].[Na+]>CN(C)C=O>[CH3:31][NH:32][C:3]([C:5]1[N:6]=[CH:7][N:8]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][C:19]=2[C:20]([F:23])([F:22])[F:21])[NH:16][C:15](=[O:24])[N:14]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])[C:13]3=[O:30])[CH:9]=1)=[O:4]

Participants

5

Reactant 3

HCID 31254N-MethylformamideHCID 10942334Sodium Methoxide2×HCID 11510616HCID 11510616, compound

Product 1

HCID 54759161HCID 54759161, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(3-methanesulfonylamino-2,4-dioxo-7-trifluoromethyl-1,2,3,4-tetrahydro -quinazolin-6-yl)-1H-imidazole-4-carboxylic acid methyl ester (800 mg, 1.79 mmol) and N-methylformamide (0.357 ml, 6 mmol) in 5 ml of dimethylformamide is heated to 120° C. and sodium methylate (100 mg, 1.79 mmol) is added under stirring. After two hours at 120° C. another 100 mg of sodium methylate is added and stirring at 120° C. continued for additional two hours. After cooling to room temperature the solution is evaporated in vacuo and the residue chromatographed to give 560 mg (1.25 mmol, 70%) of 1-(3-methanesulfonylamino-2,4-dioxo-7-trifluoromethyl-1,2,3,4-tetrahydro-quinazolin-6-yl)-1H-imidazole-4-carboxylic acid methylamide, m.p. 292 -295° C., ES-MS: m/z447 [M+H]+.

Workup

  1. stirringstirring at 120° C.
  2. customis evaporated in vacuo
  3. customthe residue chromatographed

Sources & evidence

ORD record
ord-ed9b0bc682864cb7a6bb9938d705664d
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

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