Trifluoroacetic acid → HCID 10457822, compound

HRID 425932Notes

Reaction equation

HRID 425932 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:3]=1[CH2:4][O:5][C:6]1[C:7]([NH2:21])=[N:8][CH:9]=[C:10]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[NH:17][CH:16]=[CH:15]3)[CH:11]=1.FC(F)(F)C(O)=O.[CH3:34][N:35]1[CH2:40][CH2:39][C:38](=O)[CH2:37][CH2:36]1>C(O)(=O)C>[Cl:1][C:2]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:3]=1[CH2:4][O:5][C:6]1[C:7]([NH2:21])=[N:8][CH:9]=[C:10]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[NH:17][CH:16]=[C:15]3[C:38]2[CH2:39][CH2:40][N:35]([CH3:34])[CH2:36][CH:37]=2)[CH:11]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 740491-Methyl-4-piperidoneHCID 10475090HCID 10475090, compound

Product 1

HCID 10457822HCID 10457822, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 3-(2,6-Dichloro-benzyloxy)-5-(1H-indol-5-yl)-pyridin-2-ylamine (example I-58, 200 mg, 0.52 mmol) in acetic acid (4 mL) and trifluoroacetic-acid (1 mL) was added 1-methyl-4-piperidone (0.32 mL, 2.6 mmol). The solution was refluxing for over night, and evaporated. The residue was dissolved in ethyl acetate, washed with saturated NaHCO3 and brine, dried over Na2SO4, and condensed. The crude product was purified on a silica gel column eluting with dichloromethane-methanol-triethyl amine (95:5:0.1) to provide 3-(2,6-dichloro-benzyloxy)-5-[3-(1-methyl-1,2,3,6-tetrahydro-pyridin-4-yl)-1H-indol-5-yl]-pyridin-2-ylamine (103.5 mg, 41% yield) as an orange crystalline solid.

Workup

  1. temperatureThe solution was refluxing for over night
  2. customevaporated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with saturated NaHCO3 and brine
  5. dry with materialdried over Na2SO4, and condensed
  6. customThe crude product was purified on a silica gel column
  7. washeluting with dichloromethane-methanol-triethyl amine (95:5:0.1)

Sources & evidence

ORD record
ord-50e0235368d64494a91d2b422ad80d85
Source dataset
uspto-grants-2012_01
Patent number
US08106197B2

Reaction notes

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