Trifluoroacetic acid → 7-amino-3-chloro-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one

HRID 222261ノート

反応式

HRID 222261 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[O:13])[C:11]3[CH:14]=[C:15]([NH:18]CC4C=CC(OC)=CC=4OC)[CH:16]=[CH:17][C:10]=3[CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1.FC(F)(F)C(O)=O>CO.ClCCl>[NH2:18][C:15]1[CH:16]=[CH:17][C:10]2[CH:9]=[CH:8][C:5]3=[N:6][CH:7]=[C:2]([Cl:1])[CH:3]=[C:4]3[C:12](=[O:13])[C:11]=2[CH:14]=1

参加物

5

反応物 2

HCID 6422Trifluoroacetic acidHCID 159808203-Chloro-7-[[(2,4-dimethoxyphenyl)methyl]amino]-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one

生成物 1

HCID 159808217-amino-3-chloro-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

3-chloro-7-[(2,4-dimethoxybenzyl)amino]-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one (1.1 g, 2.7 mmol) was dissolved in 8 mL methanol and 30 mL dichloromethane. Then 10 mL of trifluoroacetic acid was added and the solution was stirred at ambient temperature. After 1 hour, reaction was concentrated, dissolved in 500 mL of ethyl acetate and washed with 200 mL saturated sodium bicarbonate. The organic layer was separated, dried with magnesium sulfate, filtered, and purified by flash column chromatography (0-10% methanol/dichloromethane gradient) and reverse phase HPLC (20-100% acetonitrile/water gradient, 0.1% trifluoroacetic acid modifier) to afford title compound. LRMS (APCI) calculated for C14H10ClN2O [M+H]+, 257.0; found 257.1.

後処理

  1. customreaction
  2. concentrationwas concentrated
  3. dissolutiondissolved in 500 mL of ethyl acetate
  4. washwashed with 200 mL saturated sodium bicarbonate
  5. customThe organic layer was separated
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. custompurified by flash column chromatography (0-10% methanol/dichloromethane gradient)

出典と根拠

ORDレコード
ord-6cd29ab8117447c4bb9c4271d091a5c4
出典データセット
uspto-grants-2012_06
特許番号
US08207186B2

反応ノート

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