Methyl iodide → HCID 86604845, compound

HRID 883127Notes

Reaction equation

HRID 883127 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][C:7]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:11]([C:12]([NH:14][O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:13])[N:10]=[C:9]([C:20]2[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=2[F:27])[S:8]1)=[N+:2]=[N-:3].I[CH3:35].[H-].[Na+]>CN(C=O)C>[N:1]([CH2:4][CH2:5][CH2:6][C:7]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:11]([C:12]([N:14]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])[CH3:35])=[O:13])[N:10]=[C:9]([C:20]2[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=2[F:27])[S:8]1)=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86604846HCID 86604846, compound

Product 1

HCID 86604845HCID 86604845, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of 2-(3-azidopropyl)-N-tert-butoxy-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazole-3(2H)-carboxamide (0.061 g, 0.13 mmol) and iodomethane (0.18 g, 1.3 mmol) in DMF (4 mL) was added sodium hydride (0.006 g, 0.26 mmol). After stirring at 0° C. for 30 minutes and then at room temperature for 1 hour, the mixture was partitioned between ethyl acetate (10 mL) and saturated NH4Cl (5 mL). The organic layer was washed with water (2×5 mL), dried and concentrated under reduced pressure to provide the crude product.

Workup

  1. waitat room temperature for 1 hour
  2. customthe mixture was partitioned between ethyl acetate (10 mL) and saturated NH4Cl (5 mL)
  3. washThe organic layer was washed with water (2×5 mL)
  4. customdried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5aee84648de042d3b8433b13a5c5772a
Source dataset
uspto-grants-2012_08
Patent number
US08236825B2

Reaction notes

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