p-Toluenesulfonic acid → 4-(6-chloro-5-(2,3-difluorobenzylamino)-1,2,4-triazin-3-ylamino)-N,N-dimethylbenzamide

HRID 577427Notes

Reaction equation

HRID 577427 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([Cl:18])=[C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:11]=2[F:17])[N:7]=1.[NH2:19][C:20]1[CH:30]=[CH:29][C:23]([C:24]([N:26]([CH3:28])[CH3:27])=[O:25])=[CH:22][CH:21]=1.CC1C=CC(S(O)(=O)=O)=CC=1>CN1C(=O)CCC1>[Cl:18][C:5]1[N:4]=[N:3][C:2]([NH:19][C:20]2[CH:30]=[CH:29][C:23]([C:24]([N:26]([CH3:28])[CH3:27])=[O:25])=[CH:22][CH:21]=2)=[N:7][C:6]=1[NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:11]=1[F:17]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 2355274-Amino-N,N-dimethylbenzamideHCID 867064193,6-dichloro-N-(2,3-difluorobenzyl)-1,2,4-triazin-5-amine

Product 1

HCID 867064204-(6-chloro-5-(2,3-difluorobenzylamino)-1,2,4-triazin-3-ylamino)-N,N-dimethylbenzamideYield 53.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
105 °C

Procedure

3,6-Dichloro-N-(2,3-difluorobenzyl)-1,2,4-triazin-5-amine (75 mg, 0.26 mmol) was dissolved in 5 mL NMP. To it was added 4-amino-N,N-dimethylbenzamide (86 mg, 0.52 mmol) and pTSA (49 mg, 0.26 mmol). The mixture was stirred at 105° C. for overnight and subjected to reverse phase preparative HPLC to isolate 4-(6-chloro-5-(2,3-difluorobenzylamino)-1,2,4-triazin-3-ylamino)-N,N-dimethylbenzamide (58 mg). MS found for C19H17ClF2N6O as (M+H)+ 419.3. UV: λ=273 nm.

Sources & evidence

ORD record
ord-f55534d8a5b7445fa700f1232739c305
Source dataset
uspto-grants-2015_05
Patent number
US09040530B2

Reaction notes

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