Methyl iodide → HCID 86281677, compound

HRID 510226Notes

Reaction equation

HRID 510226 reaction equation
[NH:1]1[C:5]([C:6]2[C:7]3[CH2:15][CH2:14][N:13]([C:16]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[C:19]=4[Cl:28])=[O:17])[CH2:12][C:8]=3[N:9]=[CH:10][N:11]=2)=[CH:4][CH:3]=[N:2]1.[H-].[Na+].[CH3:31]I>CN(C=O)C.O>[Cl:28][C:19]1[C:20]([C:24]([F:25])([F:27])[F:26])=[CH:21][CH:22]=[CH:23][C:18]=1[C:16]([N:13]1[CH2:14][CH2:15][C:7]2[C:6]([C:5]3[CH:4]=[CH:3][N:2]([CH3:31])[N:1]=3)=[N:11][CH:10]=[N:9][C:8]=2[CH2:12]1)=[O:17]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86281552HCID 86281552, compound

Product 1

HCID 86281677HCID 86281677, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of Example 18 (137 mg, 0.33 mmol) in DMF (3 mL) was added NaH, 60% dispersion in mineral oil (16 mg, 0.40 mmol). After 30 minutes MeI (0.03 mL, 0.40 mmol) was then added. After several hours the reaction was diluted with water and then extracted with EtOAc. The combined organic layers were washed with water, dried over Na2SO4, filtered and concentrated in vacuo. Purification on a Prep Agilent system with a XBridge C18 OBD 50×100 mm column eluting with 5 to 99% 0.05% NH4OH in H2O/ACN over 17 min to afforded the title compound as a white solid (61.2 mg, 43%). MS (ESI) mass calcd. C19H15ClF3N5O, 421.09. m/z found 422.1 [M+H]+. 1H NMR (500 MHz, CDCl3): 9.09-8.92 (m, 1H), 7.82-7.75 (m, 1H), 7.58-7.42 (m, 3H), 7.06-7.01 (m, 1H), 5.19-4.92 (m, 1H), 4.58-4.38 (m, 1H), 4.22-3.94 (m, 4H), 3.57-3.22 (m, 3H).

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification on a Prep Agilent system with a XBridge C18 OBD 50×100 mm column
  7. washeluting with 5 to 99% 0.05% NH4OH in H2O/ACN over 17 min

Sources & evidence

ORD record
ord-c663f8dca74b4229bc7384536250981b
Source dataset
uspto-grants-2015_08
Patent number
US09096596B2

Reaction notes

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