Methyl iodide → HCID 86710411, compound

HRID 1398422Notes

Reaction equation

HRID 1398422 reaction equation
[C:1]([C:3]1[C:19]([O:20][CH2:21][C@@H:22]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:23][CH:24]([CH3:26])[CH3:25])=[CH:18][C:6]2[N:7]([CH3:17])[C:8](=[O:16])[C:9]3[C:14]([C:5]=2[CH:4]=1)=[CH:13][CH:12]=[N:11][C:10]=3[CH3:15])#[N:2].[H-].[Na+].[CH3:37]I>CN(C=O)C>[C:1]([C:3]1[C:19]([O:20][CH2:21][C@@H:22]([N:27]([CH3:37])[C:28](=[O:34])[O:29][C:30]([CH3:32])([CH3:31])[CH3:33])[CH2:23][CH:24]([CH3:26])[CH3:25])=[CH:18][C:6]2[N:7]([CH3:17])[C:8](=[O:16])[C:9]3[C:14]([C:5]=2[CH:4]=1)=[CH:13][CH:12]=[N:11][C:10]=3[CH3:15])#[N:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86710410HCID 86710410, compound

Product 1

HCID 86710411HCID 86710411, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

(S)-tert-Butyl (1-((9-cyano-4,6-dimethyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)-4-methylpentan-2-yl)carbamate (60 mg, 0.129 mmol), prepared as described in Example 64, Part B, was taken in DMF (3 mL) and cooled to 0° C. The reaction mixture was treated with NaH (10.33 mg, 0.258 mmol) followed by MeI (0.016 mL, 0.258 mmol). After stirring at 0° C. for 10 min, the reaction mixture was warmed to room temperature and stirred overnight. The mixture was then quenched with ice-cold water and extracted with ethyl acetate (2×3 mL). The combined organic layers were dried with sodium sulfate and concentrated under reduced pressure to afford (S)-tert-butyl (1-((9-cyano-4,6-dimethyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)-4-methylpentan-2-yl)(methyl)carbamate (70 mg, 0.127 mmol, 99% crude yield) as an off-white solid. The material was carried forward without further purification. LC/MS (ESI) m/e 479.2 [(M+H)+, calcd for C27H35N4O4 479.3]; LC/MS retention time (method C): tR=2.16 min.

Workup

  1. temperaturethe reaction mixture was warmed to room temperature
  2. stirringstirred overnight
  3. customThe mixture was then quenched with ice-cold water
  4. extractionextracted with ethyl acetate (2×3 mL)
  5. dry with materialThe combined organic layers were dried with sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5f150e72a38a4e79b43d25b8bbdc9fe2
Source dataset
uspto-grants-2014_12
Patent number
US08901305B2

Reaction notes

Loading…