Trifluoroacetic acid → 7-Chloro-2,6-naphthyridin-3-amine

HRID 1502416ノート

反応式

HRID 1502416 の反応式
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[C:14]([NH:19]C(=O)OC(C)(C)C)[N:15]=[CH:16]2)=[CH:11][N:10]=1>ClC(Cl)C>[Cl:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[C:14]([NH2:19])[N:15]=[CH:16]2)=[CH:11][N:10]=1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 86674971Tert-butyl 7-chloro-2,6-naphthyridin-3-ylcarbamate

生成物 1

HCID 866749727-Chloro-2,6-naphthyridin-3-amine収率 91.5%

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

実験手順

Trifluoroacetic acid (0.43 mL, 5.5 mmol) was added to a solution of tert-butyl 7-chloro-2,6-naphthyridin-3-ylcarbamate (410 mg, 1.4 mmol) in dichloroethane (7 mL). After 4 hours, the reaction mixture was concentrated in vacuo, diluted with methylene chloride (50 mL), and washed with saturated aqueous sodium bicarbonate solution (20 mL). The organic layer was separated, dried over sodium sulfate, filtered, and evaporated in vacuo to afford a residue that was purified by flash chromatography (silica, 4 g, ISCO, 0-100% ethyl acetate in heptane) to afford the title compound as a yellow solid (230 mg, 86%), which was used in the next step without further purification.

後処理

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. additiondiluted with methylene chloride (50 mL)
  3. washwashed with saturated aqueous sodium bicarbonate solution (20 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customto afford a residue that
  9. customwas purified by flash chromatography (silica, 4 g, ISCO, 0-100% ethyl acetate in heptane)

出典と根拠

ORDレコード
ord-75f02842bc244e949c940b972dfdd587
出典データセット
uspto-grants-2015_12
特許番号
US09206175B2

反応ノート

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