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

HRID 468899노트

반응식

HRID 468899 반응식
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

참가 물질

4

반응물 2

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

생성물 1

HCID 866749727-Chloro-2,6-naphthyridin-3-amine수율 91.5%

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d7ff6bf7948c4518be184c72512b9a6e
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623889B2

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