N-bromobutanimide → HCID 53466341, compound

HRID 1409283Notes

Reaction equation

HRID 1409283 reaction equation
C1C(=O)N(Br)C(=O)C1.[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:11]=1[CH:17]1[N:22]2[N:23]=[CH:24][N:25]=[C:21]2[NH:20][C:19]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)=[CH:18]1.C([O-])(O)=O.[Na+]>C(O)(C)C>[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:11]=1[C:17]1[N:22]2[N:23]=[CH:24][N:25]=[C:21]2[N:20]=[C:19]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)[CH:18]=1

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 3295594HCID 3295594, compound

Product 1

HCID 53466341HCID 53466341, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A sample of NBS (299 mg, 1.68 mmol) was added to a solution of 7-(2-Chloro-6-fluorophenyl)-5-(4-chlorophenyl)-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine (3a) (101 mg, 0.28 mmol) in isopropanol (5 mL). The reaction mixture was refluxed for 36 h, then cooled to room temperature, treated with saturated NaHCO3 solution (20 mL) and extracted with EtOAc (15 mL×3). The combined organic layer was dried over Na2SO4 and evaporated under reduced pressure. The given residue was purified through silica gel column chromatography (EtOAc/Hexanes 30:70) to afford a 42 mg white solid of 4a in 42% yield. m.p. 238-239° C. Rf=0.33 (EtOAc/Hexanes 30:70). MS: MH+=359. 1H NMR (500 MHz, CDCl3): δ 8.48 (s, 1H, CHar), 8.15 (d, J=7.5 Hz, 2H, CHar), 7.57-7.39 (m, 5H, CHar), 7.20-7.19 (m, 1H, CHar). HPLC: 97.9% (Method C, tR=5.47 min).

Workup

  1. temperatureThe reaction mixture was refluxed for 36 h
  2. extractionextracted with EtOAc (15 mL×3)
  3. dry with materialThe combined organic layer was dried over Na2SO4
  4. customevaporated under reduced pressure
  5. customThe given residue was purified through silica gel column chromatography (EtOAc/Hexanes 30:70)

Sources & evidence

ORD record
ord-33f61d110fbe4aa0875aadd295c7d4e3
Source dataset
uspto-grants-2014_12
Patent number
US08921381B2

Reaction notes

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