Sodium Sulfate → HCID 58846592, 화합물

HRID 1271705노트

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HRID 1271705 반응식
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C@@H:9]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([O:21][CH3:22])[N:19]=3)[N:14]=[CH:13][CH:12]=2)[OH:10])[CH2:4][CH2:3]1.[O:23]=[C:24]1[NH:33][C:32]2[N:31]=[CH:30][C:29]([CH:34]=O)=[CH:28][C:27]=2[CH2:26][CH2:25]1.[O-]S([O-])(=O)=O.[Na+].[Na+].[BH4-].[Na+]>ClC(Cl)C.C(O)C>[OH:10][C@H:9]([C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([O:21][CH3:22])[N:19]=2)[N:14]=[CH:13][CH:12]=1)[CH2:8][N:5]1[CH2:6][CH2:7][CH:2]([NH:1][CH2:34][C:29]2[CH:28]=[C:27]3[C:32](=[N:31][CH:30]=2)[NH:33][C:24](=[O:23])[CH2:25][CH2:26]3)[CH2:3][CH2:4]1

참가 물질

7

반응물 4

HCID 24436Sodium SulfateHCID 4311764Sodium borohydrideHCID 18454515443956-57-8HCID 23400257HCID 23400257, 화합물

생성물 1

HCID 58846592HCID 58846592, 화합물수율 21%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 63651,1-Dichloroethane용매

실험 절차

To a stirred solution of (R)-2-(4-aminopiperidin-1-yl)-1-(6-methoxy-[1,5]naphthyridin-4-yl)ethanol (2f) (0.34 g, 1.13 mmole) in dichloroethane (10 mL) and dry ethanol (5 mL) at RT was added 7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridine-3-carboxaldehyde (113 g) (0.20 g, 1.13 mmole) and granular Na2SO4 (approximately 100 mg). After 72 h, the reaction was concentrated. The remaining residue was dissolved in dry ethanol and reacted with NaBH4 (0.043 g, 1.13 mmole). After 12 h at RT, the reaction was concentrated under vacuum and the residue was dissolved in a mixture of H2O (10 mL) and saturated aqueous NaHCO3 (50 mL). The aqueous solution was extracted with EtOAc (2×75 mL) and the combined organic phases were washed with brine then were dried over Na2SO4. Flash chromatography on silica gel (9:1 CHCl3/MeOH containing 5% NH4OH) afforded the title compound (0.11 g, 21%) as a white solid: 1H NMR (400 MHz, d6-DMSO) δ 10.43 (br s, 1H), 8.77 (d, J=4.5 Hz, 1H), 8.23 (d, J=9.0 Hz, 1H), 8.01 (s, 1H), 7.75 (d, J=4.5 Hz, 1H), 7.58 (s, 1H), 7.24 (d, J=9.0 Hz, 1H), 5.77 (m, 1H), 5.23 (br s, 1H), 4.02 (s, 3H), 3.63 (s, 2H), 3.38 (m, 2H), 3.11 (m, 1H), 2.83 (m, 2H), 2.65 (m, 1H), 2.47 (m, 2H), 2.32 (m, 1H), 2.17 (m, 1H), 1.79 (m, 2H), 1.27 (m, 2H); MS (ES) m/e 463 M+H)+.

후처리

  1. concentrationthe reaction was concentrated
  2. dissolutionThe remaining residue was dissolved in dry ethanol
  3. waitAfter 12 h at RT
  4. concentrationthe reaction was concentrated under vacuum
  5. dissolutionthe residue was dissolved in a mixture of H2O (10 mL) and saturated aqueous NaHCO3 (50 mL)
  6. extractionThe aqueous solution was extracted with EtOAc (2×75 mL)
  7. washthe combined organic phases were washed with brine
  8. dry with materialthen were dried over Na2SO4

출처 및 근거

ORD 기록
ord-5e3ef9905c224588806fab61fa6f975c
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07205408B2

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