Trifluoroacetic acid → HCID 117667055, compound

HRID 1526195Notes

Reaction equation

HRID 1526195 reaction equation
[C:1]([C:4]1[N:5]=[C:6]([CH2:44][CH3:45])[C:7]([C:31]2[CH2:32][CH2:33][N:34](C(OC(C)(C)C)=O)[CH2:35][CH:36]=2)=[N:8][C:9]=1[NH:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:22][CH2:21][CH:20]([N:23]3[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]3)[CH2:19][CH2:18]2)=[C:13]([CH3:30])[CH:12]=1)(=[O:3])[NH2:2].FC(F)(F)C(O)=O>ClCCCl>[CH2:44]([C:6]1[N:5]=[C:4]([C:1]([NH2:2])=[O:3])[C:9]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:18][CH2:19][CH:20]([N:23]4[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]4)[CH2:21][CH2:22]3)=[C:13]([CH3:30])[CH:12]=2)=[N:8][C:7]=1[C:31]1[CH2:32][CH2:33][NH:34][CH2:35][CH:36]=1)[CH3:45]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117667054HCID 117667054, compound

Product 1

HCID 117667055HCID 117667055, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a mixture of tert-butyl 4-[5-carbamoyl-3-ethyl-6-({3-methyl-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)pyrazin-2-yl]-3,6-dihydropyridine-1(2H)-carboxylate (600 mg) and 1,2-dichloroethane (6 mL) was added trifluoroacetic acid (742 μL), followed by stirring at room temperature for 3 hours. The mixture was subjected to liquid separation by the addition of a 5% aqueous potassium carbonate solution and chloroform. The organic phase was washed with saturated brine and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia=1:0:0-100:10:1) to obtain 6-ethyl-3-({3-methyl-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)-5-(1,2,3,6-tetrahydropyridin-4-yl)pyrazine-2-carboxamide (460 mg) as an orange solid.

Workup

  1. customThe mixture was subjected to liquid separation by the addition of a 5% aqueous potassium carbonate solution and chloroform
  2. washThe organic phase was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia=1:0:0-100:10:1)

Sources & evidence

ORD record
ord-d69d74f5510042eca1aca79bfc964197
Source dataset
uspto-grants-2015_07
Patent number
US09085540B2

Reaction notes

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