Trifluoroacetic acid → HCID 86706417, compound

HRID 577423Notes

Reaction equation

HRID 577423 reaction equation
CS[C:3]1[N:4]=[N:5][C:6]([C:17]([NH2:19])=[O:18])=[C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[N:8]=1.C1C=C(Cl)C=C(C(OO)=O)C=1.CCN(C(C)C)C(C)C.Cl.[NH2:41][C@H:42]([CH2:46][CH3:47])[C:43]([NH2:45])=[O:44].C(O)(C(F)(F)F)=O>CN1C(=O)CCC1.O>[NH2:45][C:43](=[O:44])[C@H:42]([NH:41][C:3]1[N:4]=[N:5][C:6]([C:17]([NH2:19])=[O:18])=[C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[N:8]=1)[CH2:46][CH3:47]

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 70297m-Chloroperbenzoic acidHCID 81531DiisopropylethylamineHCID 16218339(2R)-2-aminobutanamide hydrochlorideHCID 867064153-(Methylthio)-5-(p-tolylamino)-1,2,4-triazine-6-carboxamide

Product 1

HCID 86706417HCID 86706417, compoundYield 132.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

3-(Methylthio)-5-(p-tolylamino)-1,2,4-triazine-6-carboxamide (31 mg, 0.11 mmol) was dissolved in 5 mL NMP. To it was added mCPBA (77%) (100 mg, 0.44 mmol). The mixture was stirred at RT for 1 h. To it was added DIEA (0.20 mL, 1.1 mmol) and (R)-2-aminobutanamide hydrochloride (77 mg, 0.55 mmol). The mixture was stirred at 80° C. for 2.5 h. The mixture was cooled to RT, acidified with TFA (0.3 mL), diluted with water, filtered and subjected to reverse phase preparative HPLC to isolate the title compound (48 mg) as HCl salt. MS found for C15H19N7O2 as (M+H)+ 330.4. UV: λ=235, 278 nm. Proton NMR: (CD3OD) δ 7.60 (2H, d, J=8.0 Hz), 7.28 (2H, d, J=8.0 Hz), 4.40 (1H, dd, J=8.0; 5.2 Hz), 2.36 (3H, s), 2.00 (1H, m), 1.90 (1H, m), 1.05 (3H, t, J=7.2 Hz) ppm.

Workup

  1. stirringThe mixture was stirred at 80° C. for 2.5 h
  2. temperatureThe mixture was cooled to RT
  3. filtrationfiltered

Sources & evidence

ORD record
ord-ff784fef541448fc99a72bc99a1ecc87
Source dataset
uspto-grants-2015_05
Patent number
US09040530B2

Reaction notes

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