2-Bromothiazole → HCID 59201296, compound

HRID 451710Notes

Reaction equation

HRID 451710 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C@@H:5]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=1)[C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]1.Br[C:27]1[S:28][CH:29]=[CH:30][N:31]=1>CC(O)C>[Cl:25][C:21]1[CH:20]=[C:19]([C@H:5]([O:4][CH2:3][CH2:2][NH:1][C:27]2[S:28][CH:29]=[CH:30][N:31]=2)[C@@H:6]2[CH2:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:16])[CH3:17])=[O:13])[CH2:7]2)[CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 764302-BromothiazoleHCID 59598469(R)-tert-butyl 3-((R)-(2-aminoethoxy)(3-chlorophenyl)methyl)piperidine-1-carboxylate

Product 1

HCID 59201296HCID 59201296, compoundYield 49.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A 25 mL flask was charged with (R)-tert-butyl 3-((R)-(2-aminoethoxy)(3-chlorophenyl)methyl)piperidine-1-carboxylate (100 mg, 0.27 mmol) and 2-bromo-thiazole (22 mg, 0.135 mmol) dissolved in propan-2-ol (5 mL) and stirred for 96 hr under reflux. The solvent and excess reagent was removed in vacuo to afford a residue purified by chromatography to give the pure (R)-tert-butyl 3-((R)-(3-chlorophenyl)(2-(thiazol-2-ylamino)ethoxy)methyl)piperidine-1-carboxylate (30 mg, 25%)

Workup

  1. temperatureunder reflux
  2. customThe solvent and excess reagent was removed in vacuo
  3. customto afford a residue
  4. custompurified by chromatography

Sources & evidence

ORD record
ord-fb8d40efd3404345a4a19a9d2c860d72
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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