Ammonia → Methyl 4-(6-carbamoyl-3-(methylthio)-1,2,4-triazin-5-ylamino)benzoate

HRID 1050496Notes

Reaction equation

HRID 1050496 reaction equation
Cl[C:2]1[N:3]=[C:4]([S:13][CH3:14])[N:5]=[N:6][C:7]=1[C:8]([O:10]CC)=O.[NH2:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1.C([N:29](C(C)C)CC)(C)C.N>C(#N)C>[C:8]([C:7]1[N:6]=[N:5][C:4]([S:13][CH3:14])=[N:3][C:2]=1[NH:15][C:16]1[CH:17]=[CH:18][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:24][CH:25]=1)(=[O:10])[NH2:29]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 12082Methyl 4-aminobenzoateHCID 81531DiisopropylethylamineHCID 11557703Ethyl 5-Chloro-3-(Methylthio)-1,2,4-Triazine-6-Carboxylate

Product 1

HCID 118115192Methyl 4-(6-carbamoyl-3-(methylthio)-1,2,4-triazin-5-ylamino)benzoateYield 73%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To ethyl 5-chloro-3-(methylthio)-1,2,4-triazine-6-carboxylate (1) (350 mg, 1.50 mmol) in acetonitrile (10 mL) was added methyl 4-aminobenzoate (340 mg, 2.25 mmol) and then diisopropylethylamine (DIEA, 0.39 mL, 2.25 mmol). The mixture was stirred at RT for 3 h. To the mixture was then added ammonia (7.0 N solution in methanol, 30 mL). The mixture was stirred overnight. The solid was isolated by filtration, washed with a minimum amount of cold acetonitrile and then washed with hexane. The solid was dried in a vacuum oven to afford methyl 4-(6-carbamoyl-3-(methylthio)-1,2,4-triazin-5-ylamino)benzoate (2) (348 mg, 73% yield) in high purity.

Workup

  1. stirringThe mixture was stirred overnight
  2. customThe solid was isolated by filtration
  3. washwashed with a minimum amount of cold acetonitrile
  4. washwashed with hexane
  5. customThe solid was dried in a vacuum oven

Sources & evidence

ORD record
ord-ec38c1442b70458ea94c089ef47d0741
Source dataset
uspto-grants-2016_07
Patent number
US09382246B2

Reaction notes

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