Chloroform → HCID 131730964, compound

HRID 2035502Notes

Reaction equation

HRID 2035502 reaction equation
[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:28][CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)=[CH:18][CH:17]=2)[N:12]=[CH:11][C:10]=1[CH2:29][C:30]([NH2:32])=[O:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:33](=O)([O-])[O-].[K+].[K+].IC.C(Cl)(Cl)Cl>CN(C)C=O>[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([NH:15][C:16]2[CH:17]=[CH:18][C:19]([N:22]3[CH2:28][CH2:27][CH2:26][N:25]([CH3:33])[CH2:24][CH2:23]3)=[CH:20][CH:21]=2)[N:12]=[CH:11][C:10]=1[CH2:29][C:30]([NH2:32])=[O:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 131730953HCID 131730953, compound2×

Product 1

HCID 131730964HCID 131730964, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

25 mg of 4-(benzylamino)-6-{[4-(1,4-diazepan-1-yl)phenyl]amino}pyridine-3-carboxyamide (the compound of Example 226) was dissolved in 0.3 mL of N,N-dimethylformamide, to which, under ice cooling, 10 mg of potassium carbonate and 4.3 mg of iodomethane were added, and stirred at the same temperature for 30 minutes and at room temperature for further 30 minutes. To the reaction mixture, chloroform was added, and the insoluble substances were filtered off. The solvent was evaporated and the residue was purified by silica gel thin layer chromatography (chloroform:ammonia methanol=10:1) to obtain 9 mg (35%) of the title compound as a light brown solid.

Workup

  1. filtrationthe insoluble substances were filtered off
  2. customThe solvent was evaporated
  3. customthe residue was purified by silica gel thin layer chromatography (chloroform:ammonia methanol=10:1)

Sources & evidence

ORD record
ord-f46e3a6879414ce18ede5be50f895787
Source dataset
uspto-grants-2013_11
Patent number
US08575153B2

Reaction notes

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