(5-Ethyl-2-methyl-2H-pyrazol-3-yl)-carbamic acid phenyl ester → 1-{(S)-3-[3-(4-Chloro-phenoxy)-azetidin-1-yl]-1-methoxymethyl-propyl}-3-(5-ethyl-2-methyl-2H-pyrazol-3-yl)-urea

HRID 1182134Notes

Reaction equation

HRID 1182134 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][CH:7]2[CH2:10][N:9]([CH2:11][CH2:12][C@H:13]([NH2:17])[CH2:14][O:15][CH3:16])[CH2:8]2)=[CH:4][CH:3]=1.C1([O:26][C:27](=O)[NH:28][C:29]2[N:30]([CH3:36])[N:31]=[C:32]([CH2:34][CH3:35])[CH:33]=2)C=CC=CC=1>CS(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]2[CH2:10][N:9]([CH2:11][CH2:12][C@H:13]([NH:17][C:27]([NH:28][C:29]3[N:30]([CH3:36])[N:31]=[C:32]([CH2:34][CH3:35])[CH:33]=3)=[O:26])[CH2:14][O:15][CH3:16])[CH2:8]2)=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 69360901(5-Ethyl-2-methyl-2H-pyrazol-3-yl)-carbamic acid phenyl esterHCID 69410633(S)-3-[3-(4-Chloro-phenoxy)-azetidin-1-yl]-1-methoxymethyl-propylamine

Product 1

HCID 102382381-{(S)-3-[3-(4-Chloro-phenoxy)-azetidin-1-yl]-1-methoxymethyl-propyl}-3-(5-ethyl-2-methyl-2H-pyrazol-3-yl)-urea

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of (S)-3-[3-(4-Chloro-phenoxy)-azetidin-1-yl]-1-methoxymethyl-propylamine (1.6 g, 5.6 mmol) and (5-Ethyl-2-methyl-2H-pyrazol-3-yl)-carbamic acid phenyl ester (1.65 g, 6.7 mmol, see preparation below) in DMSO (7 ml) is stirred at ambient temperature for 4 hours, then partitioned between water and ethylacetate. The organic phase is washed again with water, dried over MgSO4 and evaporated. The crude product is purified by flash silica chromatography (elution with a 5:95 methanol/dichloromethane) to afford 1-{(S)-3-[3-(4-Chloro-phenoxy)-azetidin-1-yl]-1-methoxymethyl-propyl}-3-(5-ethyl-2-methyl-2H-pyrazol-3-yl)-urea. [M+H] 436.37.

Workup

  1. custompartitioned between water and ethylacetate
  2. washThe organic phase is washed again with water
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customThe crude product is purified by flash silica chromatography (
  6. washelution with a 5:95 methanol/dichloromethane)

Sources & evidence

ORD record
ord-aef89875428b4aaeaec7ba8aa79dc3b0
Source dataset
uspto-grants-2007_10
Patent number
US07288537B2

Reaction notes

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