Methyl iodide → HCID 66613589, compound

HRID 510078Notes

Reaction equation

HRID 510078 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[F:27])[N:12]=2)[N:8]=[C:7]2[C:3]=1[NH:4][C:5](=[S:28])[NH:6]2.[C:29](=O)([O-])[O-].[K+].[K+].IC>CN(C)C=O>[F:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[CH2:20][N:13]1[C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:19]2[C:11]([C:9]2[N:8]=[C:7]3[C:3]([NH:4][C:5]([S:28][CH3:29])=[N:6]3)=[C:2]([NH2:1])[N:10]=2)=[N:12]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 86720050HCID 86720050, compound

Product 1

HCID 66613589HCID 66613589, compoundYield 17.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

100 mg (0.255 mmol) of the compound from example 28 were dissolved in 5 ml of dimethylformamide, and 49 mg (0.357 mmol) of potassium carbonate were added. The mixture was heated to 70° C. for 10 min and, after cooling, 18 μl (0.291 mmol) of iodomethane were added and the mixture was stirred at RT for 48 h. The mixture was concentrated and the residue was taken up in water and acidified with acetic acid. A solid precipitates out, which was filtered off and washed with water. The purification was effected by means of preparative HPLC (eluent: methanol/water, gradient 30:70→90:10). 18 mg of the title compound were obtained (17% of theory).

Workup

  1. temperatureafter cooling
  2. concentrationThe mixture was concentrated
  3. customA solid precipitates out, which
  4. filtrationwas filtered off
  5. washwashed with water
  6. customThe purification

Sources & evidence

ORD record
ord-b5a23a201f264be4a55e5ce5f6590cca
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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