Triethylamine → HCID 11662582, compound

HRID 2069291Notes

Reaction equation

[CH3:1][S:2]([NH:5][N:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][C:11]([C:25]([F:28])([F:27])[F:26])=[C:12]([N:17]3[CH:21]=[C:20]([C:22]([OH:24])=O)[N:19]=[CH:18]3)[CH:13]=2)[NH:8][C:7]1=[O:29])(=[O:4])=[O:3].Cl.[CH3:31][NH:32][CH3:33].ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C=O>[CH3:31][N:32]([CH3:33])[C:22]([C:20]1[N:19]=[CH:18][N:17]([C:12]2[CH:13]=[C:14]3[C:9](=[CH:10][C:11]=2[C:25]([F:26])([F:28])[F:27])[NH:8][C:7](=[O:29])[N:6]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])[C:15]3=[O:16])[CH:21]=1)=[O:24]

Participants

Conditions

Temperature: 100 °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 (120 mg, 0.277 mmol) in 10 ml of dimethylformamide is treated with dimethylamine hydrochloride (46 mg, 0.554 mmol), N-3-dimethylaminopropyl-N′-ethyl-carbodiimide hydrochloride (60 mg, 0.305 mmol), N-hydroxybenzotriazole (11 mg, 0.08 mmol) and triethylamine (0.1 ml, 0.72 mmol). The solution is heated to 100° C. for 1 hour, cooled to room temperature, evaporated in vacuo and the residue chromatographed over silica gel to give 22 mg (0.048 mmoles, 17%) of 1-(3-methanesulfonylamino-2,4-dioxo-7-trifluoromethyl-1,2,3,4-tetrahydro-quinazolin-6-yl)-1H -imidazole-4-carboxylic acid dimethylamide, m.p. 284 -286° C., ES-MS: m/z 461 [M+H]+.

Workup

temperaturecooled to room temperature
customevaporated in vacuo
customthe residue chromatographed over silica gel

Sources & evidence

ORD record: ord-2b7146fc21154428ba98d3f2cf2bcaf3
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299085B2

Reaction notes

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