Hydrogen Bromide → HCID 54759530, compound

HRID 538887Notes

Reaction equation

HRID 538887 reaction equation
[CH2:1]([CH:3]([CH2:20][CH3:21])[CH:4]([C:10]1[CH:19]=[CH:18][C:13]2[N:14]=[C:15](N)[S:16][C:12]=2[CH:11]=1)[N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1)[CH3:2].[BrH:22].N([O-])=O.[Na+].C([O-])(O)=O.[Na+]>O.CC#N>[Br:22][C:15]1[S:16][C:12]2[CH:11]=[C:10]([CH:4]([N:5]3[CH:9]=[CH:8][N:7]=[CH:6]3)[CH:3]([CH2:20][CH3:21])[CH2:1][CH3:2])[CH:19]=[CH:18][C:13]=2[N:14]=1

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 547595316-(2-ethyl-1-(1H-imidazol-1-yl)butyl)benzo[d]thiazol-2-amine

Product 1

HCID 54759530HCID 54759530, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 6-(2-ethyl-1-(1H-imidazol-1-yl)butyl)benzo[d]thiazol-2-amine (260 mg, 0.866 mmol) and water (4 mL) at 0° C. was added aqueous HBr (0.98 mL, 8.66 mmol) and the mixture was cooled to −0° C. A cold (−10° C.) solution of sodium nitrite (75 mg, 1.08 mmol) in water (1 mL) was added to the reaction mixture over a period of 5 min while maintaining the temperature below −5° C. and the reaction was stirred at −10° C. for 15 min. To a cold (−10° C.) solution of CuBr2 (253 mg, 1.08 mmol) in water (4 mL) was added the reaction mixture and stirred for 10 min at 0° C. MeCN was added to the reaction mixture and then the reaction mixture was stirred for 2.5 h while warming to RT. The reaction was basified with sat. aq. NaHCO3 (pH 7) and then 10 N NaOH (pH 8) followed by celite filtration. The aqueous phase was extracted three times with DCM and the organic extracts were combined and dried over MgSO4, filtered and then concentrated. The crude product was purified by preparative TLC using 5% MeOH in DCM as eluent to afford to 2-bromo-6-(2-ethyl-1-(1H-imidazol-1-yl)butyl)benzo[d]thiazole as white solid. MS (ES+): m/z 364 (MH+).

Workup

  1. temperaturewhile maintaining the temperature below −5° C.
  2. stirringstirred for 10 min at 0° C
  3. stirringthe reaction mixture was stirred for 2.5 h
  4. temperaturewhile warming to RT
  5. filtration10 N NaOH (pH 8) followed by celite filtration
  6. extractionThe aqueous phase was extracted three times with DCM
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product was purified by preparative TLC

Sources & evidence

ORD record
ord-7a4c03084db6417a81a7b1c9ab005e4a
Source dataset
uspto-grants-2014_10
Patent number
US08865752B2

Reaction notes

Loading…