(2-Bromoethyl)cyclohexane → HCID 140660332, compound

HRID 1528345Notes

Reaction equation

HRID 1528345 reaction equation
[CH3:1][N:2]1[C:6](=[O:7])[O:5][N:4]=[C:3]1/[C:8](=[N:15]\[O:16][CH2:17][C:18]1[N:23]=[C:22]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH:21]=[CH:20][CH:19]=1)/[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[H-].[Na+].Br[CH2:35][CH2:36][CH:37]1[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1>CN(C)C=O>[CH:37]1([CH2:36][CH2:35][N:24]([C:22]2[CH:21]=[CH:20][CH:19]=[C:18]([CH2:17][O:16]/[N:15]=[C:8](\[C:3]3[N:2]([CH3:1])[C:6](=[O:7])[O:5][N:4]=3)/[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:23]=2)[C:25](=[O:31])[O:26][C:27]([CH3:28])([CH3:30])[CH3:29])[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1

Participants

5

Reactant 3

HCID 15440(2-Bromoethyl)cyclohexaneHCID 24758Sodium hydrideHCID 140660330HCID 140660330, compound

Product 1

HCID 140660332HCID 140660332, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of tert-butyl {6-[({[(Z)-(4-methyl-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate (100 mg, 0.235 mmol, 1 eq.) in N,N-dimethylformamide (2 ml) was treated with sodium hydride (10 mg, 0.259 mmol, 1.1 eq.) and stirred at room temperature for 30 minutes. (2-Bromoethyl)cyclohexane (67 mg, 0.353 mmol, 1.5 eq.) was than added and stirring was allowed overnight. The reaction was quenched by addition of water and extracted with EtOAc (3×20 ml). The organics were combined, washed with aq. sat. NaCl, dried over MgSO4 and concentrated to afford tert-butyl (2-cyclohexylethyl){6-[({[(Z)-(4-methyl-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate (108 mg, 86% yield) which was used in the next step without further purification.

Workup

  1. additionthan added
  2. stirringstirring
  3. waitwas allowed overnight
  4. customThe reaction was quenched by addition of water
  5. extractionextracted with EtOAc (3×20 ml)
  6. washwashed with aq. sat. NaCl
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-11c6da25468f4522badd0764753ff5ab
Source dataset
uspto-grants-2015_07
Patent number
US09090600B2

Reaction notes

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