Acetonitrile → HCID 67236140, compound

HRID 447162Notes

Reaction equation

HRID 447162 reaction equation
Br[C:2]1[S:3][C:4]2[CH:10]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.[C:16]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].C(=O)([O-])[O-].[K+].[K+].C(#N)C>O>[C:19]([O:18][C:16]([N:23]1[CH2:28][CH2:27][N:26]([C:2]2[S:3][C:4]3[CH:10]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:8]=[CH:7][C:5]=3[N:6]=2)[CH2:25][CH2:24]1)=[O:17])([CH3:22])([CH3:20])[CH3:21]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 12067225Ethyl 2-bromo-6-benzothiazolecarboxylate

Product 1

HCID 67236140HCID 67236140, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The ethyl 2-bromobenzo[d]thiazole-6-carboxylate (11.1 g), BOC-piperazine (9.03 g), potassium carbonate (11.7 g) and acetonitrile (400 mL) were combined and heated to reflux overnight. The resulting mixture was cooled to room temperature, diluted with water and extracted with EtOAc. The organics were concentrated to a yellow solid, which was recrystallized from EtOAc/heptane to yield a ethyl 2-(4-(tert-butoxycarbonyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylate as a white powder, which was collected by filtration.

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. extractionextracted with EtOAc
  4. concentrationThe organics were concentrated to a yellow solid, which
  5. customwas recrystallized from EtOAc/heptane

Sources & evidence

ORD record
ord-8e2213134dff4b08987d2115cf97cac5
Source dataset
uspto-grants-2013_07
Patent number
US08481547B2

Reaction notes

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