Sodium Sulfate → HCID 58846592、化合物

HRID 1271705ノート

反応式

HRID 1271705 の反応式
[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

参加物

7

反応物 4

HCID 24436Sodium SulfateHCID 4311764Sodium borohydrideHCID 18454515443956-57-8HCID 23400257HCID 23400257、化合物

生成物 1

HCID 58846592HCID 58846592、化合物収率 21%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 63651,1-Dichloroethane溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-5e3ef9905c224588806fab61fa6f975c
出典データセット
uspto-grants-2007_04
特許番号
US07205408B2

反応ノート

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