Trifluoroacetic acid → HCID 178518093, compound

HRID 1024198Notes

Reaction equation

HRID 1024198 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][NH:7][C:8]2[N:13]=[C:12](Cl)[C:11]([CH:15]([C:17]3[C:25]4[C:20](=[N:21][CH:22]=[CH:23][CH:24]=4)[NH:19][CH:18]=3)O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=[O:38]>C(#N)C>[NH:19]1[C:20]2=[N:21][CH:22]=[CH:23][CH:24]=[C:25]2[C:17]([CH2:15][C:11]2[C:12]([OH:38])=[N:13][C:8]([NH:7][CH2:6][C:5]3[CH:26]=[CH:27][C:2]([Cl:1])=[CH:3][CH:4]=3)=[CH:9][CH:10]=2)=[CH:18]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 59593284HCID 59593284, compound

Product 1

HCID 178518093HCID 178518093, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

To (6-(4-chlorobenzylamino)-2-chloropyridin-3-yl)(1H-pyrrolo[2,3-b]pyridin-3-yl)methanol (P-0050, 0.028 g, 0.000070 mol) dissolved in acetonitrile (1 mL) was added triethylsilane (42.6 uL, 0.000266 mol) and trifluoroacetic acid (28.4 uL, 0.000368 mol). The reaction was heated at 85° C. overnight. The reaction was extracted with ethyl acetate and saturated sodium bicarbonate. The organic layer was separated, dried over magnesium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with dichloromethane, 3%, 5% and finally 10% methanol in dichloromethane to give the compound as a white solid (P-0051, 20 mg, 78%). MS (ESI) [M+H+]+=365.3.

Workup

  1. extractionThe reaction was extracted with ethyl acetate and saturated sodium bicarbonate
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. custompurified by silica gel column chromatography
  7. washeluting with dichloromethane, 3%, 5% and finally 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-78cde25b2c344e999ffc9ef4118f4b87
Source dataset
uspto-grants-2014_05
Patent number
US08722702B2

Reaction notes

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