Formamide → HCID 11711704, compound

HRID 2069293Notes

Reaction equation

C[O:2][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.C([NH2:33])=O.C[O-].[Na+]>CN(C)C=O>[CH3:29][S:26]([NH:25][N:14]1[C:13](=[O:30])[C:12]2[C:17](=[CH:18][C:19]([C:20]([F:22])([F:21])[F:23])=[C:10]([N:8]3[CH:9]=[C:5]([C:3]([NH2:33])=[O:2])[N:6]=[CH:7]3)[CH:11]=2)[NH:16][C:15]1=[O:24])(=[O:27])=[O:28]

Participants

Conditions

Temperature: 120 °C

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 (50 mg, 0.112 mmol) and formamide (0.15 ml, 0.374 mmol) in 5 ml of dimethylformamide is heated to 120° C. and sodium methylate (6 mg, 0.112 mmol) is added under stirring. After two hours at 120° C. the solution is cooled to room temperature, evaporated in vacuo and the residue chromatographed to give 30 mg (0.069 mmol, 62%) of amorphous 1-(3-methanesulfonylamino-2,4-dioxo-7-trifluoromethyl-1,2,3,4-tetrahydro-quinazolin-6-yl)-1H -imidazole-4-carboxylic acid amide, ES-MS: m/z 433 [M+H]+.

Workup

customevaporated in vacuo
customthe residue chromatographed

Sources & evidence

ORD record: ord-273ac7087f6a4fe7aa7537c99ce61aa1
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299085B2

Reaction notes

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