Sodium borohydride → HCID 59176564, compound

HRID 628692Notes

Reaction equation

HRID 628692 reaction equation
[NH2:1][C@H:2]([C:15](=[O:24])[NH:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11].[N:25]1[C:34]2[C:33](=O)[CH2:32][CH2:31][CH2:30][C:29]=2[CH:28]=[CH:27][CH:26]=1.[BH4-].[Na+]>C(O)C.C([O-])(O)=O.[Na+]>[O:24]=[C:15]([NH:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)[C@@H:2]([NH:1][CH:33]1[C:34]2[N:25]=[CH:26][CH:27]=[CH:28][C:29]=2[CH2:30][CH2:31][CH2:32]1)[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11]

Participants

6

Reactant 3

HCID 4311764Sodium borohydrideHCID 117447776,7-Dihydro-5H-quinoline-8-oneHCID 59176420HCID 59176420, compound

Product 1

HCID 59176564HCID 59176564, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of (S)-tert-butyl 5-amino-6-oxo-6-(pyridin-2-ylmethyl-amino)hexylcarbamate, 28, (2.16 g, 6.43 mmol) in ethanol (14 mL) was added 6,7-dihydroquinolin-8(5H)-one (0.90 g, 6.12 mmol). The mixture was heated in microwave reactor at 150° C. for 13 min. After cooling the reaction to room temp., NaBH4 (0.46 g, 12.24 mmol) was added to the mixture. The reaction mixture was stirred at room temp for 1 h. The mixture was diluted with aqueous saturated NaHCO3, extracted twice with ethyl acetate. The organic phase was dried (MgSO4), filtered and concentrated in vacuo. The crude residue was purified by silica gel chromatography (5% to 25% methanol/CH2Cl2) to afford the desired product 29: 1H NMR (d6-DMSO) δ 8.44 (d, J=4.4 Hz, 1H), 8.40 (m, 1H), 8.32-8.31 (m, 1H), 7.66 (t, J=7.2 Hz, 1H), 7.45 (d, J=7.6 Hz, 1H), 7.24 (d, J=8.0 Hz, 1H), 7.20 (t, J=4.8 Hz, 1H), 7.13 (dd, J=8.0, 4.2 Hz, 1H), 6.94 (d, J=7.6 Hz, 1H), 4.32 (d, J=5.6 Hz, 2H), 3.95-3.89 (m, 1H), 3.62-3.57 (m, 1H), 2.69 (d, J=4.8 Hz, 2H), 2.61-2.56 (m, 2H), 1.99-1.95 (m, 1H), 1.89-1.83 (m, 1H), 1.63-1.28 (m, 8H), 1.35 (s, 9H); ESI+ MS: m/z (rel intensity) 468.3 (100, [M+H]+).

Workup

  1. temperatureAfter cooling
  2. customthe reaction to room temp.
  3. extractionextracted twice with ethyl acetate
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by silica gel chromatography (5% to 25% methanol/CH2Cl2)

Sources & evidence

ORD record
ord-5d06422b012f43b48f107c168d1416c8
Source dataset
uspto-grants-2016_04
Patent number
US09314468B2

Reaction notes

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