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Hydrochloric Acid → (S)-ethyl 6-bromo-4-oxo-1-(piperidin-3-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylate

HRID 1047158
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HRID 1047158 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[N:8]([C@H:12]1[CH2:17][CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13]1)[CH:7]=[C:6]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:5]2=[O:30].Cl.O1CCOCC1>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[N:8]([C@H:12]1[CH2:17][CH2:16][CH2:15][NH:14][CH2:13]1)[CH:7]=[C:6]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:5]2=[O:30]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 68796045(S)-ethyl 6-bromo-1-(1-(tert-butoxycarbonyl)piperidin-3-yl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate2회

생성물 1

HCID 69621276(S)-ethyl 6-bromo-4-oxo-1-(piperidin-3-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(S)-ethyl 6-bromo-1-(1-(tert-butoxycarbonyl)piperidin-3-yl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate (Intermediate 30, 10.847 g, 22.58 mmol) was taken up in dichloromethane (10 mL) and added HCl 4M in Dioxane (113 mL, 451.63 mmol) while stirring at RT for 1 h. The solvent was removed in vacuo and the residue was triturated with DCM, ether and EtOAc to give the desired product as a yellow solid. (S)-ethyl 6-bromo-4-oxo-1-(piperidin-3-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylate (8.50 g, 90%) was recovered as the HCl salt. MS (ES)(M+H)+: 381 for C16H18BrN3O3.[HCl].

후처리

  1. customThe solvent was removed in vacuo
  2. customthe residue was triturated with DCM, ether and EtOAc

출처 및 근거

ORD 기록
ord-614eafb8d6ef44d4b2873e968ba61b9d
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08569484B2

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