Dimethylformamide → HCID 89442949, compound

HRID 2283943Notes

Reaction equation

HRID 2283943 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)[N:5]([CH2:7][CH2:8]OS(C)(=O)=O)[CH:6]=1.[NH:27]1[CH2:30][CH2:29][CH2:28]1.CN(C=O)C>CC(=O)OCC>[N:27]1([CH2:8][CH2:7][N:5]2[CH:6]=[C:2]([Br:1])[N:3]=[C:4]2[CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)[CH2:30][CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 10422AzetidineHCID 86641601tert-butyl 4-(4-bromo-1-(2-((methylsulfonyl)oxy)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylate

Product 1

HCID 89442949HCID 89442949, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A reaction mixture of tert-butyl 4-(4-bromo-1-(2-((methylsulfonyl)oxy)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylate (28.0 g) and azetidine (11 ml) in to DMF (200 ml) was stirred at 50° C. overnight. The reaction was diluted with EA, washed with water followed by saturated aqueous sodium chloride, dried and concentrated. The residue was purified by column chromatography to give tert-butyl 4-(1-(2-(azetidin-1-yl)ethyl)-4-bromo-1H-imidazol-2-yl)piperidine-1-carboxylate as off-white solid. (17.2 g).

Workup

  1. washwashed with water
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-806a3a3e177a41c086fa74df8ccb8d25
Source dataset
uspto-grants-2015_09
Patent number
US09145392B2

Reaction notes

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