Tetrahydrofuran → 9-bromo-6-{[(1R)-2-methyl-1-(trifluoromethyl)propyl]amino}benzo[c]-1,6-naphthyridin-1(2H)-one

HRID 2192962노트

반응식

HRID 2192962 반응식
[Br:1][C:2]1[CH:25]=[CH:24][C:5]2[C:6]([NH:15][C@@H:16]([C:20]([F:23])([F:22])[F:21])[CH:17]([CH3:19])[CH3:18])=[N:7][C:8]3[C:13]([C:4]=2[CH:3]=1)=[C:12](Cl)[N:11]=[CH:10][CH:9]=3.C1C[O:29]CC1>Cl.CCOC(C)=O>[Br:1][C:2]1[CH:25]=[CH:24][C:5]2[C:6]([NH:15][C@@H:16]([C:20]([F:23])([F:22])[F:21])[CH:17]([CH3:19])[CH3:18])=[N:7][C:8]3[CH:9]=[CH:10][NH:11][C:12](=[O:29])[C:13]=3[C:4]=2[CH:3]=1

참가 물질

5

반응물 2

HCID 8028TetrahydrofuranHCID 593755309-bromo-1-chloro-N-[(1R)-2-methyl-1-(trifluoromethyl)propyl]benzo[c]-1,6-naphthyridin-6-amine

생성물 1

HCID 249053779-bromo-6-{[(1R)-2-methyl-1-(trifluoromethyl)propyl]amino}benzo[c]-1,6-naphthyridin-1(2H)-one

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 8857Ethyl Acetate용매2회

실험 절차

9-bromo-1-chloro-N-[(1R)-2-methyl-1-(trifluoromethyl)propyl]benzo[c]-1,6-naphthyridin-6-amine (1.0 g, 2.31 mmol) in 6 N HCl (4 mL) and THF (4 mL) was heated to 90° C. for 2 hr. The reaction was cooled and diluted with EtOAc and quenched with sat. NaHCO3. The mixture was extracted and the organic layers were separated, dried with MgSO4, filtered, and concentrated to give the crude product. Column chromatography on silica gel 100% Hex. to 100% EtOAc afforded 9-bromo-6-{[(1R)-2-methyl-1-(trifluoromethyl)propyl]amino}benzo[c]-1,6-naphthyridin-1(2H)-one. 1H NMR (600 MHz, CD3OD) δ 10.1 (d, 1H), 8.31 (d, 1H), 7.75 (d, 1H), 7.40 (d, 1H), 6.65, (d, 1H), 5.46 (m, 1H), 2.35 (m, 1H), 1.12 (d, 3H), 1.06 (d, 3H). LRMS (ESI) calc'd for (C17H16BrF3N3O) [M+H]+, 414.0; found 414.0.

후처리

  1. temperatureThe reaction was cooled
  2. customquenched with sat. NaHCO3
  3. extractionThe mixture was extracted
  4. customthe organic layers were separated
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the crude product

출처 및 근거

ORD 기록
ord-efe21f3b208d4767a03cff0712b273f6
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08329722B2

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