N-bromobutanimide → HCID 178492795, compound

HRID 1158095Notes

Reaction equation

HRID 1158095 reaction equation
[CH3:1][CH:2]([CH:4]1[S:8][C:7]([NH:9][C:10]23[CH2:19][CH:14]4[CH2:15][CH:16]([CH2:18][CH:12]([CH2:13]4)[CH2:11]2)[CH2:17]3)=[N:6][C:5]1=[O:20])[CH3:3].C1C(=O)N(Br)[C:23](=[O:24])C1>C(Cl)(Cl)(Cl)Cl>[CH:2]([C:4]1([O:24][CH3:23])[S:8][C:7]([NH:9][C:10]23[CH2:19][CH:14]4[CH2:13][CH:12]([CH2:18][CH:16]([CH2:15]4)[CH2:17]2)[CH2:11]3)=[N:6][C:5]1=[O:20])([CH3:1])[CH3:3]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 178440508HCID 178440508, compound

Product 1

HCID 178492795HCID 178492795, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 5-(1-methylethyl)-2-(tricyclo[3.3.1.13,7]dec-1-ylamino)-1,3-thiazol-4(5H)-one (146 mg, 0.5 mmol) and NBS (107 mg, 0.6 mmol) in CCl4 (60 mL) was stirred at reflux for 30 min. The resulting mixture was cooled to 0° C., and filtered to remove the solid. The residue was then concentrated in vacuo and diluted with CH2Cl2 (20 mL). To this mixture was added MeOH (200 uL) and DIEA (200 uL). The mixture was stirred for 30 min, then was concentrated in vacuo and purified by flash chromatography (4:1; Hexane:EtOAc) to give the title compound as white solid. MS (ES+): 323 (M+H)+.

Workup

  1. temperatureat reflux for 30 min
  2. filtrationfiltered
  3. customto remove the solid
  4. concentrationThe residue was then concentrated in vacuo
  5. additiondiluted with CH2Cl2 (20 mL)
  6. additionTo this mixture was added MeOH (200 uL) and DIEA (200 uL)
  7. stirringThe mixture was stirred for 30 min
  8. concentrationwas concentrated in vacuo
  9. custompurified by flash chromatography (4:1; Hexane:EtOAc)

Sources & evidence

ORD record
ord-2c17c3a677904c06bdf3e20ed4f355f4
Source dataset
uspto-grants-2010_10
Patent number
US07807700B2

Reaction notes

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