Sodium hydride → (S)-tert-butyl (4-methyl-1-((5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)pentan-2-yl)carbamate

HRID 1398286Notes

Reaction equation

HRID 1398286 reaction equation
[H-].[Na+].[C:3]([C:6]1[CH:7]=[N:8][CH:9]=[CH:10][C:11]=1[C:12]1[CH:32]=[CH:31][C:15]([O:16][CH2:17][C@@H:18]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:19][CH:20]([CH3:22])[CH3:21])=[CH:14][C:13]=1F)(=[O:5])[NH2:4]>O1CCCC1>[CH3:21][CH:20]([CH3:22])[CH2:19][C@H:18]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:17][O:16][C:15]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][N:8]=[CH:9][CH:10]=3)[C:3](=[O:5])[NH:4][C:32]=2[CH:31]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 86710302(S)-tert-butyl (1-(4-(3-carbamoylpyridin-4-yl)-3-fluorophenoxy)-4-methylpentan-2-yl)carbamate

Product 1

HCID 86710303(S)-tert-butyl (4-methyl-1-((5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)pentan-2-yl)carbamateYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Sodium hydride (5.56 mg, 0.232 mmol, 60% in mineral oil) was taken in tetrahydrofuran (1 mL) and cooled to 0° C. The suspension was treated with (S)-tert-butyl (1-(4-(3-carbamoylpyridin-4-yl)-3-fluorophenoxy)-4-methylpentan-2-yl)carbamate (50 mg, 0.116 mmol) in THF (1 mL) dropwise and the temperature was maintained at 0° C. for 30 min. The reaction mixture was then allowed to warm to room temperature and stirred for 2 h. The reaction was quenched with ice and extracted with ethyl acetate (3×5 mL). The combined organic layers were washed with brine (1×5 mL), dried (Na2SO4) and concentrated under reduced pressure to afford (S)-tert-butyl (4-methyl-1-((5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)pentan-2-yl)carbamate (40 mg, 0.097 mmol, 84% yield) as a colorless solid. LC/MS (ESI) m/e 412.2 [(M+H)+, calcd for C23H30N3O4 412.2]; LC/MS retention time (method C): tR=1.97 min.

Workup

  1. temperaturethe temperature was maintained at 0° C. for 30 min
  2. temperatureto warm to room temperature
  3. customThe reaction was quenched with ice
  4. extractionextracted with ethyl acetate (3×5 mL)
  5. washThe combined organic layers were washed with brine (1×5 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-16f03acd4a344858aeb0cae4272add32
Source dataset
uspto-grants-2014_12
Patent number
US08901305B2

Reaction notes

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