Ammonia → HCID 86628204, compound

HRID 1821360Notes

Reaction equation

HRID 1821360 reaction equation
C(O[CH:4]=[CH:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])C.BrN1C(=O)CCC1=O.[NH:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21](/[CH:28]=[CH:29]/[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[NH:36][C:37]([NH2:39])=[S:38])=[N:20]1.N>O1CCOCC1.O>[CH2:9]([O:8][C:6]([C:5]1[S:38][C:37]([NH:36][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2/[CH:29]=[CH:28]/[C:21]2[C:22]3[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=3)[NH:19][N:20]=2)=[N:39][CH:4]=1)=[O:7])[CH3:10]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 67184N-bromobutanimideHCID 221780Ethyl 3-ethoxy-2-propenoateHCID 86628203HCID 86628203, compound

Product 1

HCID 86628204HCID 86628204, compoundYield 8.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Ethyl 3-ethoxyacrylate (0.22 mL, 1.5 mmol) was dissolved in dioxane (4.0 mL) and water (4.0 mL) and after cooling to −10° C., the solution was added with N-bromosuccinimide (0.29 g, 1.6 mmol), followed by stirring at room temperature for 1 hour. The mixture was added with Compound 161 (0.40 g, 1.4 mmol), followed by stirring at 80° C. for 1 hour. The reaction mixture was added with aqueous ammonia to stop the reaction. The precipitated crude product was collected by filtration, purified by silica gel column chromatography (hexane/ethyl acetate=4/1 to 1/2) and triturated in ethyl acetate to obtain Compound 165 (45 mg, 8%).

Workup

  1. stirringby stirring at 80° C. for 1 hour
  2. customthe reaction
  3. customThe precipitated crude product
  4. filtrationwas collected by filtration
  5. custompurified by silica gel column chromatography (hexane/ethyl acetate=4/1 to 1/2)
  6. customtriturated in ethyl acetate

Sources & evidence

ORD record
ord-706c1e2918694ca39b6eac0ca6e6e88e
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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