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

HRID 249710ノート

反応式

HRID 249710 の反応式
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

参加物

8

反応物 4

HCID 10476Cyanogen BromideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 67273317HCID 67273317、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1140Toluene溶媒HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6c1e5ec583304f4fb221a93d0576852c
出典データセット
uspto-grants-2011_01
特許番号
US07863269B2

反応ノート

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