Methyl iodide → HCID 66619845, compound

HRID 415562Notes

Reaction equation

HRID 415562 reaction equation
[S:1]=[C:2]1[NH:14][C:5]2[CH:6]=[N:7][C:8]3[CH:9]=[CH:10][CH:11]=[N:12][C:13]=3[C:4]=2[N:3]1[CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21].[OH-].[NH4+].I[CH3:28]>O.C(O)C>[CH3:28][S:1][C:2]1[N:3]([CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:23])[CH3:22])[C:4]2[C:13]3[N:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=[CH:6][C:5]=2[N:14]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14923Ammonium HydroxideHCID 86633747HCID 86633747, compound

Product 1

HCID 66619845HCID 66619845, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

tert-Butyl 2-(2-thioxo-2,3-dihydro-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethylcarbamate (31 g, 89.8 mmol) in water (150 mL) and ethanol (150 mL) was treated with ammonium hydroxide (30 mL) and iodomethane (25.5 g, 180 mmol) according to the general method of Part E of Example 22. After three hours, most of the ethanol was removed under reduced pressure, and water (500 mL) was added to the resulting suspension. The mixture was allowed to stand for 30 minutes. A solid was present and was isolated by filtration, washed with water and diethyl ether, and dried under vacuum for three hours to provide tert-butyl 2-[2-(methylthio)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]ethylcarbamate as a white solid.

Workup

  1. custommost of the ethanol was removed under reduced pressure, and water (500 mL)
  2. additionwas added to the resulting suspension
  3. waitto stand for 30 minutes
  4. customwas isolated by filtration
  5. washwashed with water and diethyl ether
  6. customdried under vacuum for three hours

Sources & evidence

ORD record
ord-4ed034f4c1ef4bdfad41ed97e7082cb0
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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