Cyanogen Bromide → Methyl 3-aminoimidazo[1,5-a]pyridine-6-carboxylate

HRID 249710Notes

Reaction equation

HRID 249710 reaction equation
FC(F)(F)C(O)=O.[NH2:8][CH2:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][N:11]=1.C[CH2:21][N:22](C(C)C)C(C)C.N#CBr.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.C(#N)C.O>[NH2:22][C:21]1[N:11]2[CH:12]=[C:13]([C:14]([O:16][CH3:17])=[O:15])[CH:18]=[CH:19][C:10]2=[CH:9][N:8]=1

Participants

8

Reactant 4

HCID 10476Cyanogen BromideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 67273317HCID 67273317, compound

Product 1

HCID 57791295Methyl 3-aminoimidazo[1,5-a]pyridine-6-carboxylate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Procedure

Methyl 6-aminomethylnicotinate trifluoroacetate (390 mg) was dissolved in toluene (35 ml) and treated with Hünig's base (230 μl). Cyanogen bromide (0.35 ml of a 5 M solution in acetonitrile) was then slowly added dropwise. After stirring at RT for 3 h, the solvent was stripped off and the residue was taken up with water and saturated sodium hydrogencarbonate solution and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated. The residue was purified by means of preparative HPLC. The product-containing fractions were combined, freed from the acetonitrile and freeze-dried. The residue was then taken up with a little water, treated with saturated sodium hydrogencarbonate solution and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated. 110 mg of the desired compound were obtained.

Workup

  1. extractionextracted three times with ethyl acetate
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by means of preparative HPLC
  6. customfreeze-dried
  7. additiontreated with saturated sodium hydrogencarbonate solution
  8. extractionextracted three times with ethyl acetate
  9. dry with materialThe combined organic phases were dried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-6c1e5ec583304f4fb221a93d0576852c
Source dataset
uspto-grants-2011_01
Patent number
US07863269B2

Reaction notes

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