Acetic Acid → HCID 178428704, compound

HRID 505401Notes

Reaction equation

HRID 505401 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:9](/[CH:11]=[CH:12]/[C:13]3[N:18]=[C:17]([NH2:19])[CH:16]=[C:15]([CH3:20])[CH:14]=3)[NH:8][C:5]2=[N:6][CH:7]=1.C(O)(=O)C>CO.O=[Pt]=O>[NH2:19][C:17]1[CH:16]=[C:15]([CH3:20])[CH:14]=[C:13]([CH2:12][CH2:11][C:9]2[NH:8][C:5]3=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=[C:4]3[N:10]=2)[N:18]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 178428702HCID 178428702, compound

Product 1

HCID 178428704HCID 178428704, compoundYield 73.7%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

930 mg of 6-[(E)-2-(6-bromo-3H-imidazo[4,5-b]pyridin-2-yl)-vinyl]-4-methyl-pyridin-2-ylamine (compound A11) are suspended in 300 ml of methanol. Subsequently, 805 μl acetic acid and 96 mg of Adam's catalyst [platin(IV) oxide] are added. The suspension is vigorously stirred for 65 h. Thereafter, the solution is passed through kieselguhr, which is rinsed with methanol. The filtrate is evaporated to dryness and the remaining residue (1.20 g) purified by chromatography on silica gel (eluent: dichloromethane/methanol=20:1) to afford 690 mg of the title compound as colorless powder after lyophilization from 15.0 ml dioxane and 3.0 ml water. M.p. 216° C. ESI-MS: 332.1/334.2 (MH+, 97%/100%). TLC: Rf=0.35 (dichloromethane/methanol 10:1).

Workup

  1. washis rinsed with methanol
  2. customThe filtrate is evaporated to dryness
  3. customthe remaining residue (1.20 g) purified by chromatography on silica gel (eluent: dichloromethane/methanol=20:1)

Sources & evidence

ORD record
ord-20d04c38cdc1464ea28a6dfc04d05075
Source dataset
uspto-grants-2010_08
Patent number
US07781453B2

Reaction notes

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