Potassium Carbonate → Trifluoroacetic acid

HRID 2207407Notes

Reaction equation

HRID 2207407 reaction equation
Cl.[NH2:2][OH:3].[C:4](=[O:7])([O-])[O-:5].[K+].[K+].[CH3:10][C:11]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[C:26]([NH:28][C:29]3[N:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=[CH:31][N:30]=3)[CH:25]=[C:24]([CH3:39])[CH:23]=2)=[CH:18][N:17]=1)([CH3:14])[C:12]#[N:13]>C(O)C.CS(C)=O>[OH:3]/[N:2]=[C:12](\[NH2:13])/[C:11]([CH3:10])([NH:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[C:26]([NH:28][C:29]3[N:34]=[C:33]([C:35]([F:37])([F:36])[F:38])[CH:32]=[CH:31][N:30]=3)[CH:25]=[C:24]([CH3:39])[CH:23]=2)=[CH:18][N:17]=1)[CH3:14].[C:4]([OH:5])([C:35]([F:38])([F:37])[F:36])=[O:7]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 118092776HCID 118092776, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 118092577HCID 118092577, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

Hydroxylamine hydrochloride (101 mg, 1.46 mmol) and potassium carbonate (201 mg, 1.46 mmol) were added to a mixture of 2-methyl-2-{[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-2-yl]amino}propanenitrile (100 mg, 0.242 mmol) in ethanol (404 μL). The reaction stirred at 85° C. overnight. The reaction mixture was diluted with DMSO, filtered, and purified by reverse phase HPLC (5-95% acetonitrile in water+0.5% TFA) to yield (1Z)—N′-hydroxy-2-methyl-2-{[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-2-yl]amino}propanimidamide as a bis-TFA salt. MS APCI calc'd for C21H23F3N7O [M+H]+ 446. found 446.

Workup

  1. filtrationfiltered
  2. custompurified by reverse phase HPLC (5-95% acetonitrile in water+0.5% TFA)

Sources & evidence

ORD record
ord-7f33a5f514734a9d859eefb96e807a7c
Source dataset
uspto-grants-2016_06
Patent number
US09376418B2

Reaction notes

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