Methyl iodide → HCID 21254871, compound

HRID 636376Notes

Reaction equation

HRID 636376 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:12]=[CH:11][N:10]([CH3:13])[N:9]=2)[CH:5]=[CH:4][C:3]=1[C:14]([C:16]1[C:26]2[NH:25][C:24]3[N:27]=[CH:28][CH:29]=[CH:30][C:23]=3[CH2:22][NH:21][C:20]=2[CH:19]=[CH:18][CH:17]=1)=[O:15].[CH3:31]CCCCC.[H-].[Na+].CI>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:12]=[CH:11][N:10]([CH3:13])[N:9]=2)[CH:5]=[CH:4][C:3]=1[C:14]([C:16]1[C:26]2[NH:25][C:24]3[N:27]=[CH:28][CH:29]=[CH:30][C:23]=3[CH:22]([CH3:31])[NH:21][C:20]=2[CH:19]=[CH:18][CH:17]=1)=[O:15]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8058HexaneHCID 24758Sodium hydrideHCID 21996863HCID 21996863, compound

Product 1

HCID 21254871HCID 21254871, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under anhydrous conditions, a solution of [2-chloro-4-(1-methyl-1H-pyrazol-3-yl)-phenyl]-(5,11-dihydro-pyrido[2,3-b][1,5]benzodiazepin-10-yl)-methanone of Example 19 (0.382 g, 0.92 mmol) in 10 mL of tetrahydrofuran was added dropwise to a stirred slurry of hexane washed sodium hydride (0.025 g, 1.02 mmol) in 2 mL of tetrahydrofuran. After the gas evolution ceased, methyl iodide (1 mL) was added and stirring was continued for 2 hours. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine and dried over sodium sulfate. The solvent was removed and the crude product purified by flash chromatography (on silica Merck-60, dichloromethane-ethyl acetate 2:1) to give the title compound (0.18 g, 47%). Crystallization from diethylether provided a light yellow solid (0.16 g), m.p. 249-250° C.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed
  5. customthe crude product purified by flash chromatography (on silica Merck-60, dichloromethane-ethyl acetate 2:1)

Sources & evidence

ORD record
ord-a35ebed9ca7b4240ad93ae8ea3f5fb2e
Source dataset
uspto-grants-2001_02
Patent number
US06194407B1

Reaction notes

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