Methyl iodide → HCID 22710962, compound

HRID 352966Notes

Reaction equation

HRID 352966 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[NH:14][C:15]([C:17]([N:19]3[CH2:24][CH2:23][N:22]([S:25]([C:28]4[CH:37]=[CH:36][C:35]5[C:30](=[CH:31][CH:32]=[C:33]([Cl:38])[CH:34]=5)[CH:29]=4)(=[O:27])=[O:26])[CH2:21][CH2:20]3)=[O:18])=[CH:16][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:41]I.[Cl-].[NH4+]>CN(C)C=O.O.C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[N:14]([CH3:41])[C:15]([C:17]([N:19]3[CH2:24][CH2:23][N:22]([S:25]([C:28]4[CH:37]=[CH:36][C:35]5[C:30](=[CH:31][CH:32]=[C:33]([Cl:38])[CH:34]=5)[CH:29]=4)(=[O:26])=[O:27])[CH2:21][CH2:20]3)=[O:18])=[CH:16][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 22710430HCID 22710430, compound

Product 1

HCID 22710962HCID 22710962, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(t-butoxycarbonyl)-2-[[4-[(6-chloronaphthalen-2-yl)sulfonyl]piperazin-1-yl]carbonyl]-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine (33.0 mg) in N,N-dimethylformamide (15 ml), sodium hydride (60% in oil, 3.5 mg) was added at 0° C. After stirring for 10 minutes, methyl iodide (4.5 μl) was added and the resulting mixture was stirred at 0° C. for 1 hour. To the reaction mixture, a saturated aqueous solution (10 ml) of ammonium chloride, methylene chloride (20 ml) and water (30 ml) were added to separate the organic layer. The resulting water layer was extracted with methylene chloride (10 ml). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by preparative thin-layer chromatography on a silica gel (methylene chloride:acetone=9:1), whereby the title compound (32.3 mg) was obtained as a colorless, transparent viscous substance.

Workup

  1. stirringthe resulting mixture was stirred at 0° C. for 1 hour
  2. customto separate the organic layer
  3. extractionThe resulting water layer was extracted with methylene chloride (10 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by preparative thin-layer chromatography on a silica gel (methylene chloride:acetone=9:1), whereby the title compound (32.3 mg)
  7. customwas obtained as a colorless, transparent viscous substance

Sources & evidence

ORD record
ord-b104118f0bab4287abaaf799042df6f0
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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