N-bromobutanimide → HCID 44553770, compound

HRID 1958466Notes

Reaction equation

HRID 1958466 reaction equation
C(O/[CH:4]=[CH:5]\[C:6]1[CH:7]=[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[N:10]([CH:12]=[N:13][N:14]=2)[CH:11]=1)C.C1C(=O)N(Br)C(=O)C1.[CH2:29]([NH:32][C:33]([NH2:35])=[S:34])[CH2:30][CH3:31]>O1CCOCC1.O>[C:15]1([C:8]2[C:9]3[N:10]([CH:12]=[N:13][N:14]=3)[CH:11]=[C:6]([C:5]3[S:34][C:33]([NH:32][CH2:29][CH2:30][CH3:31])=[N:35][CH:4]=3)[CH:7]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 67184N-bromobutanimideHCID 1615208Propyl-2-thioureaHCID 58207976(Z)-6-(2-ethoxyvinyl)-8-phenyl-[1,2,4]triazolo[4,3-a]pyridine

Product 1

HCID 44553770HCID 44553770, compoundYield 27.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of (Z)-6-(2-ethoxyvinyl)-8-phenyl-[1,2,4]triazolo[4,3-a]pyridine (13 mg, 0.049 mmol) in 1,4-dioxane (1 mL) and water (1 mL) was added NBS (9.4 mg, 0.054 mmol) and stirred at rt for 1 h. The mixture was then added 1-propylthiourea (6.4 mg, 0.054 mmol), heated to 85-90° C. for 10 h, then cooled and concentrated. The residue was dissolved in a mixture of 20% MeOH in dichloromethane and purified by 500 μm silica gel prep plate using 75% ethyl acetate in hexanes as an eluent. The product was collected (4.5 mg, 27.4% yield). LCMS: 336.55 (M+H), Tr 2.98 min, (Conditions A).

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in a mixture of 20% MeOH in dichloromethane
  4. custompurified by 500 μm silica gel prep plate
  5. customThe product was collected (4.5 mg, 27.4% yield)
  6. custom336.55 (M+H), Tr 2.98 min

Sources & evidence

ORD record
ord-65a5e54c33ea47fe92ad5714ae69d2c4
Source dataset
uspto-grants-2013_04
Patent number
US08410128B2

Reaction notes

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