Potassium Carbonate → HCID 9946340, compound

HRID 431958Notes

Reaction equation

HRID 431958 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:11]=[C:10]([C:12]2[CH:17]=[C:16]([OH:18])[CH:15]=[C:14]([C:19]#[N:20])[CH:13]=2)[O:9][N:8]=1.[C:21](=O)([O-])[O-].[K+].[K+].Cl.[CH3:28][N:29]([CH3:34])[CH:30](C)[CH2:31]Cl>CN(C)C=O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:11]=[C:10]([C:12]2[CH:17]=[C:16]([O:18][CH2:21][CH2:31][CH2:30][N:29]([CH3:34])[CH3:28])[CH:15]=[C:14]([C:19]#[N:20])[CH:13]=2)[O:9][N:8]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 284272-Propanamine, 1-chloro-N,N-dimethyl-, hydrochloride (1:1)HCID 9878436HCID 9878436, compound

Product 1

HCID 9946340HCID 9946340, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a similar fashion, 3-(2-pyridyl)-5-(3-cyano-5-hydroxyphenyl) -1,2,4-oxadiazole (31 mg, 0.12 mmol), potassium carbonate (381mg, 2.8 mmol) and 2-dimethylaminopropyl chloride hydrochloride (51 mg, 0.32 mmol) in N,N-dimethylformamide (1 mL) were heated in a sealed vial at 150° C. for 5 minutes. Standard work up and chromatography afforded 10 mg (24%) of 3-(2-pyridyl)-5-(3-cyano-5-(dimethylaminopropoxy)phenyl) -1,2,4-oxadiazole: 1H NMR (CDCl3): δ-8.86 (d, 1H), 8.23 (d, 1H), 8.14 (s, 1H), 8.03 (s, 1H), 7.91 (t, 1H), 7.49 (m, 1H), 7.41 (s, 1H), 4.17 (t, 2H), 2.49 (t, 2H), 2.28 (s, 6H), 2.02 (q, 2H).

Sources & evidence

ORD record
ord-8f6cdc86799d4a1fb1732b0e94e669eb
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Reaction notes

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