Methylamine → HCID 11712010, compound

HRID 2069266Notes

Reaction equation

HRID 2069266 reaction equation
C(O[C:4]([C:6]1[N:10]=[CH:9][N:8]([C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][C:20]=2[C:21]([F:24])([F:23])[F:22])[NH:17][C:16](=[O:25])[N:15]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])[C:14]3=[O:31])[N:7]=1)=[O:5])C.[CH3:32][NH2:33]>CO.C(O)C>[CH3:32][NH:33][C:4]([C:6]1[N:10]=[CH:9][N:8]([C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][C:20]=2[C:21]([F:22])([F:24])[F:23])[NH:17][C:16](=[O:25])[N:15]([NH:26][S:27]([CH3:30])(=[O:28])=[O:29])[C:14]3=[O:31])[N:7]=1)=[O:5]

Participants

5

Reactant 2

HCID 6329MethylamineHCID 11503584HCID 11503584, compound

Product 1

HCID 11712010HCID 11712010, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A solution of 150 mg (0.324 mmol) of 1-(3-methanesulfonylamino-2,4-dioxo-7-trifluoromethyl-1,2,3,4-tetrahydro-quinazolin-6-yl)-1H-[1,2,4]triazole-3-carboxylic acid ethyl ester in 0.8 ml of methanol is treated with 0.40 ml (3.24 mmol) of a ˜8M methylamine solution in ethanol. The mixture is stirred for 22 hours at room temperature and then concentrated in vacuo. The crude product is taken up in water and the pH of the solution is adjusted to 3 with 1 M aqueous HCl solution and the mixture is stirred for 3 hours at 0° C. The crystals are filtered, washed with cold water and dried in vacuo to give 124 mg (86%) of 1-(3-methanesulfonylamino-2,4-dioxo-7-trifluoromethyl-1,2,3,4-tetrahydro-quinazolin-6-yl)-1H-[1,2,4]triazole-3-carboxylic acid methylamide as white crystals, m.p. 257-260° C.

Workup

  1. concentrationconcentrated in vacuo
  2. stirringthe mixture is stirred for 3 hours at 0° C
  3. filtrationThe crystals are filtered
  4. washwashed with cold water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-6b7a9731297f48c9bf287bb3717fc8bb
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

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