Phenacyl bromide → HCID 22459784, compound

HRID 2185103Notes

Reaction equation

HRID 2185103 reaction equation
[O:1]1[C:5]([C:6]2[CH:11]=[CH:10][C:9]([NH:12][C:13]([NH2:15])=[NH:14])=[CH:8][C:7]=2[O:16][CH3:17])=[CH:4][N:3]=[CH:2]1.[CH2:18](Br)[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=O>CN(C)C=O>[CH3:17][O:16][C:7]1[CH:8]=[C:9]([NH:12][C:13]2[NH:15][C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:18][N:14]=2)[CH:10]=[CH:11][C:6]=1[C:5]1[O:1][CH:2]=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 178493224HCID 178493224, compound

Product 1

HCID 22459784HCID 22459784, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product of Example 243, Part A, 4-Oxazol-5-yl-3-methoxyphenylguanidine, 243A (150 mg, 0.65 mmol) and phenacylbromide (128 mg, 0.65 mmol) were dissolved in N,N-dimethylformamide (0.25 mL) and stirred at room temperature for 3 days. The reaction mixture was evaporated and purified by prep RPHPLC to yield 5 mg (2%, a significant portion of the product was spilled during isolation) of the title compound. LCMS conditions J, retention time=1.62 min, (90%), M+H+=333.17. (100%).

Workup

  1. customThe reaction mixture was evaporated
  2. custompurified by prep RPHPLC
  3. customto yield 5 mg (2%

Sources & evidence

ORD record
ord-e8d83732956e4eb889a3e183969e0173
Source dataset
uspto-grants-2002_06
Patent number
US06399773B1

Reaction notes

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