(S)-2-amino-4-[3-(4-chlorophenoxy)-azetidin-1-yl]-butan-1-ol → 1-{(S)-3-[3-(4-Chloro-phenoxy)-azetidin-1-yl]-1-hydroxymethyl-propyl}-3-(5-ethyl-2-methyl-2H-pyrazol-3-yl)-urea

HRID 1182136Notes

Reaction equation

HRID 1182136 reaction equation
[NH2:1][C@@H:2]([CH2:5][CH2:6][N:7]1[CH2:10][CH:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[CH2:8]1)[CH2:3][OH:4].C1([O:25][C:26](=O)[NH:27][C:28]2[N:29]([CH3:35])[N:30]=[C:31]([CH2:33][CH3:34])[CH:32]=2)C=CC=CC=1>CS(C)=O>[Cl:18][C:15]1[CH:14]=[CH:13][C:12]([O:11][CH:9]2[CH2:10][N:7]([CH2:6][CH2:5][C@H:2]([NH:1][C:26]([NH:27][C:28]3[N:29]([CH3:35])[N:30]=[C:31]([CH2:33][CH3:34])[CH:32]=3)=[O:25])[CH2:3][OH:4])[CH2:8]2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 11184815(S)-2-amino-4-[3-(4-chlorophenoxy)-azetidin-1-yl]-butan-1-olHCID 69360901(5-Ethyl-2-methyl-2H-pyrazol-3-yl)-carbamic acid phenyl ester

Product 1

HCID 102878861-{(S)-3-[3-(4-Chloro-phenoxy)-azetidin-1-yl]-1-hydroxymethyl-propyl}-3-(5-ethyl-2-methyl-2H-pyrazol-3-yl)-urea

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of (S)-2-amino-4-[3-(4-chloro-phenoxy)-azetidin-1-yl]-butan-1-ol (0.45 g, 2 mmol) and (5-Ethyl-2-methyl-2H-pyrazol-3-yl)-carbamic acid phenyl ester (0.49 g, 1.66 mmol) in DMSO (5 ml) is stirred at ambient temperature for 1 hour, then partitioned between water and ethylacetate. The organic phase is dried over MgSO4 and evaporated. The crude product is purified by recrystallisation from hot ethylacetate to afford 1-{(S)-3-[3-(4-Chloro-phenoxy)-azetidin-1-yl]-1-hydroxymethyl-propyl}-3-(5-ethyl-2-methyl-2H-pyrazol-3-yl)-urea.

Workup

  1. custompartitioned between water and ethylacetate
  2. dry with materialThe organic phase is dried over MgSO4
  3. customevaporated
  4. customThe crude product is purified by recrystallisation from hot ethylacetate

Sources & evidence

ORD record
ord-d254f30ebd844962a1cda36f7be047e6
Source dataset
uspto-grants-2007_10
Patent number
US07288537B2

Reaction notes

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