Pyridine → HCID 69491452, compound

HRID 1296757Notes

Reaction equation

HRID 1296757 reaction equation
[NH2:1][C:2]1[CH:22]=[C:21]([C:23]2[N:27]=[C:26]([CH3:28])[O:25][N:24]=2)[CH:20]=[CH:19][C:3]=1[CH2:4][NH:5][C:6](=[O:18])[C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([CH3:15])=[C:9]([O:16][CH3:17])[CH:8]=1.[N:29]1C=CC=[CH:31][CH:30]=1.Br.BrCCN.[OH-].[Na+]>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[NH2:29][CH2:30][CH2:31][NH:1][C:2]1[CH:22]=[C:21]([C:23]2[N:27]=[C:26]([CH3:28])[O:25][N:24]=2)[CH:20]=[CH:19][C:3]=1[CH2:4][NH:5][C:6](=[O:18])[C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([CH3:15])=[C:9]([O:16][CH3:17])[CH:8]=1

Participants

8

Reactant 4

HCID 1049PyridineHCID 14798Sodium HydroxideHCID 27742172-Bromoethylamine hydrobromide2×HCID 69491883N-[2-Amino-4-(5-methyl-[1,2,4]oxadiazol-3-yl)-benzyl]-3,5-dimethoxy-4-methyl-benzamide

Product 1

HCID 69491452HCID 69491452, compoundYield 49.4%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of compound 1g (114 mg, 0.3 mmol) and pyridine (0.049 mL, 0.60 mmol) in DMF was added 2-bromoethylamine hydrobromide (92 mg, 0.45 mmol). The reaction mixture was heated at 80° C. for three days. After two days, additional 2-bromoethylamine hydrobromide (100 mg) and tetrabutylammonium iodide (5 mg) was added. The reaction was diluted with water and made basic by addition of 1 N NaOH. The solid was recovered by filtration and washed with water. The solid was purified by preparative thin layer chromatography (9:1 chloroform/methanol) to give compound 44a (63 mg, 49%). ESI-MS m/e 426.3 (M+1).

Workup

  1. filtrationThe solid was recovered by filtration
  2. washwashed with water
  3. customThe solid was purified by preparative thin layer chromatography (9:1 chloroform/methanol)

Sources & evidence

ORD record
ord-4ca86f5d45d14f2692398926a9a64a40
Source dataset
uspto-grants-2007_07
Patent number
US07247654B2

Reaction notes

Loading…