Methyl iodide → HCID 21027774, compound

HRID 1385122Notes

Reaction equation

HRID 1385122 reaction equation
[Na].[Cl:2][C:3]1[CH:4]=[N:5][CH:6]=[C:7]([Cl:28])[C:8]=1[NH:9][C:10]([C:12]1[CH:20]=[C:19]2[C:15]([C:16]([CH2:26][CH3:27])=[N:17][N:18]2[CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:14][CH:13]=1)=[O:11].I[CH3:30]>CN(C=O)C.O>[Cl:28][C:7]1[CH:6]=[N:5][CH:4]=[C:3]([Cl:2])[C:8]=1[N:9]([CH3:30])[C:10]([C:12]1[CH:20]=[C:19]2[C:15]([C:16]([CH2:26][CH3:27])=[N:17][N:18]2[CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:14][CH:13]=1)=[O:11]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 5360545SodiumHCID 9822424HCID 9822424, compound

Product 1

HCID 21027774HCID 21027774, compoundYield 52.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

5.2 mg (0.130 mmol, 1.05 equiv) sodium hybride, 60% oil dispersion, were added to a room temperature solution of 50 mg (0.124 mmol, 1.0 equiv) 1-cyclopentyl-3-ethyl-1H-indazole-6-carboxylic acid (3,5-dichlor-pyridin-4-yl)-amide in 3 mL anhydrous DMF. After 30 min. 7.7 μl (0.124 mmol, 1.0 equiv) iodomethane were added and the mixture stirred at room temperature for 4 h. The reaction mixture was diluted with 50 mL H2O and extracted 2×20 mL ethyl acetate. The ethyl acetate extracts were combined, washed 2×5 mL H2O, 1×5 mL brine, and dried over Na2SO4. Filtration, concentration of filtrate and drying gave a yellow oil, which was purified on a silica gel column (25% ethylacetate/hexanes, flash) to give 27 mg (52%) of a white crystalline solid: mp 118-119° C.; HRMS calcd for C21H22N4OCl3+H: 417.12519. Found: 417.12270.

Workup

  1. extractionextracted 2×20 mL ethyl acetate
  2. washwashed 2×5 mL H2O, 1×5 mL brine
  3. dry with materialdried over Na2SO4
  4. filtrationFiltration, concentration of filtrate
  5. customdrying
  6. customgave a yellow oil, which
  7. customwas purified on a silica gel column (25% ethylacetate/hexanes, flash)

Sources & evidence

ORD record
ord-9e056440c10f4342b76bedaf5bed86b4
Source dataset
uspto-grants-2001_07
Patent number
US06262040B1

Reaction notes

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