Methyl iodide → HCID 11632959, compound

HRID 1686036Notes

Reaction equation

HRID 1686036 reaction equation
[H-].[Na+].[CH2:3]([C:10]1[C:14]2[C:15]([NH:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)=[N:16][CH:17]=[CH:18][C:13]=2[NH:12][C:11]=1[CH3:28])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.I[CH3:30]>CN(C)C=O.C(OCC)(=O)C>[ClH:27].[CH2:3]([C:10]1[C:14]2[C:15]([NH:19][CH2:20][C:21]3[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=3)=[N:16][CH:17]=[CH:18][C:13]=2[N:12]([CH3:30])[C:11]=1[CH3:28])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11553043HCID 11553043, compound

Product 1

HCID 11632959HCID 11632959, compoundYield 58.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound (30 mg, 0.12 mmol) prepared in Example 73 was treated with a saturated sodium bicarbonate solution to obtain 3-benzyl-2-methyl-4-(4-chlorobenzylamino)-1H-pyrrolo[3,2-c]pyridine (24 mg, 0.065 mmol). Sodium hydride (60%, 4.9 mg, 0.118 mmol) was added at room temperature to a solution of 3-benzyl-2-methyl-4-(4-chlorobenzylamino)-1H-pyrrolo[3,2-c]pyridine (24 mg, 0.065 mmol) in N,N-dimethylformamide (1 ml) and then the reaction mixture was stirred for 30 minutes. Iodomethane (0.007 ml, 0.118 mmol) was added to the reaction mixture, which was then stirred for 1 hour at room temperature. The reaction mixture was diluted with ethyl acetate (10 ml) and washed with water (10 ml) three times. The separated organic layer was dried on anhydrous magnesium sulfate, and then concentrated. The resulting residue was dissolved in ethyl acetate (1 ml), saturated with hydrochloric acid gas, and then filtered to give the titled compound as a white solid. (Yield: 58.2%)

Workup

  1. stirringwas then stirred for 1 hour at room temperature
  2. washwashed with water (10 ml) three times
  3. dry with materialThe separated organic layer was dried on anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. dissolutionThe resulting residue was dissolved in ethyl acetate (1 ml), saturated with hydrochloric acid gas
  6. filtrationfiltered

Sources & evidence

ORD record
ord-24c108fc23024e2b986cfd8d2b3460f6
Source dataset
uspto-grants-2012_04
Patent number
US08148529B2

Reaction notes

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