Iodoethane → HCID 66614186, compound

HRID 510080Notes

Reaction equation

HRID 510080 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(=O)([O-])[O-].[K+].[K+].I[CH2:36][CH3:37]>CN(C)C=O>[CH2:36]([S:28][C:5]1[NH:4][C:3]2[C:7](=[N:8][C:9]([C:11]3[C:19]4[C:14](=[N:15][CH:16]=[CH:17][CH:18]=4)[N:13]([CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[F:27])[N:12]=3)=[N:10][C:2]=2[NH2:1])[N:6]=1)[CH3:37]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 86720050HCID 86720050, compound

Product 1

HCID 66614186HCID 66614186, compoundYield 56.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

150 mg (0.382 mmol) of the compound from example 28 were dissolved in 2 ml of dimethylformamide, and 58 mg (0.420 mmol) of potassium carbonate were added. The mixture was heated to 70° C. for 10 min and, after cooling, 31 μl (0.382 mmol) of iodoethane were added and the mixture was stirred at RT for 16 h. The mixture was concentrated, and the residue was adsorbed on silica gel and purified by means of chromatography on silica gel (eluent: dichloromethane/methanol=20:1). 91 mg of the title compound were obtained (51% of theory).

Workup

  1. temperatureafter cooling
  2. concentrationThe mixture was concentrated
  3. custompurified by means of chromatography on silica gel (eluent: dichloromethane/methanol=20:1)

Sources & evidence

ORD record
ord-4d1df71b45a74cab929f3013ad7b07d9
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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