Potassium Carbonate → HCID 136358423, compound

HRID 601367Notes

Reaction equation

HRID 601367 reaction equation
[CH:1]1([CH2:4][NH:5][N:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([OH:16])=[C:8]([C:17]3[NH:22][C:21]4[CH:23]=[CH:24][C:25]([OH:27])=[CH:26][C:20]=4[S:19](=[O:29])(=[O:28])[N:18]=3)[C:7]2=[O:30])[CH2:3][CH2:2]1.Cl.[CH2:32]([N:39]1[CH:43]=[CH:42][N:41]=[C:40]1[CH2:44]Cl)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:32]([N:39]1[CH:43]=[CH:42][N:41]=[C:40]1[CH2:44][O:27][C:25]1[CH:24]=[CH:23][C:21]2[NH:22][C:17]([C:8]3[C:7](=[O:30])[N:6]([NH:5][CH2:4][CH:1]4[CH2:2][CH2:3]4)[C:15]4[C:10]([C:9]=3[OH:16])=[CH:11][CH:12]=[CH:13][CH:14]=4)=[N:18][S:19](=[O:28])(=[O:29])[C:20]=2[CH:26]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27792431-benzyl-2-(chloromethyl)-1H-imidazole hydrochlorideHCID 136358401HCID 136358401, compound

Product 1

HCID 136358423HCID 136358423, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

Product of Example 320C (20 mg, 0.047 mmol) in N,N-dimethylformamide (1 mL) was was heated with 1-benzyl-2-(chloromethyl)-1H-imidazole hydrochloride (23 mg, 0.095 mmol), potassium carbonate (0.061 g, 0.187 mmol) and tetrabutylammonium iodide (catalytic) at 120° C. for 2 hours in a microwave reactor. The solution was cooled to 25° C. and concentrated. The residue was triturated with ethyl acetate, filtered and washed with water to give title compound (21 mg, 75%).

Workup

  1. concentrationconcentrated
  2. customThe residue was triturated with ethyl acetate
  3. filtrationfiltered
  4. washwashed with water

Sources & evidence

ORD record
ord-b8be13c0b01849368bddb7721b3ba610
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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