Hydrochloric Acid → (3R)-3-[(9-fluoro-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridin-6-yl)amino]piperidinium chloride

HRID 2192973ノート

反応式

HRID 2192973 の反応式
[Cl:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:5]=1[C:6](Cl)=[N:7]2.[NH2:18][C@@H:19]1[CH2:24][CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20]1.Cl.[O:33]1CCOCC1>C1COCC1>[Cl-:1].[F:17][C:15]1[CH:14]=[CH:13][C:5]2[C:6]([NH:18][C@@H:19]3[CH2:24][CH2:23][CH2:22][NH2+:21][CH2:20]3)=[N:7][C:8]3[CH:9]=[CH:10][NH:11][C:2](=[O:33])[C:3]=3[C:4]=2[CH:16]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 1501974tert-butyl (3R)-3-aminopiperidine-1-carboxylateHCID 59375375HCID 59375375、化合物

生成物 1

HCID 67416365(3R)-3-[(9-fluoro-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridin-6-yl)amino]piperidinium chloride

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
125 °C

実験手順

To a solution of 1,6-dichloro-9-fluorobenzo[c]-1,6-naphthyridine (320 mg, 1.2 mmol) in dioxane (8 mL) was added tert-butyl (3R)-3-aminopiperidine-1-carboxylate (960 mg, 4.79 mmol) and heated in a microwave reactor for 1 hr at 125° C. The solution was concentrated to provide the crude solid. The crude material was dissolved in THF (5 mL) and 6 N HCl 5 mL) and heated to 85° C. for 2 hr. Upon cooling the solution solidifies and the reaction mixture was triturated with Et2O and filtered to afford (3R)-3-[(9-fluoro-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridin-6-yl)amino]piperidinium chloride. LRMS (ESI) calc'd for (C17H18FN4O) [M+H]+, 313.2; found 313.1.

後処理

  1. concentrationThe solution was concentrated
  2. customto provide the crude solid
  3. temperatureUpon cooling the solution
  4. customthe reaction mixture was triturated with Et2O
  5. filtrationfiltered

出典と根拠

ORDレコード
ord-2ced445b9f6b473eb8d9b46a16720eb2
出典データセット
uspto-grants-2012_12
特許番号
US08329722B2

反応ノート

読み込み中…