(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-cyclopropyl-2-methyl-2H-pyrazol-3-yl)-urea

HRID 1182135Notes

Reaction equation

HRID 1182135 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]([CH3:36])[N:30]=[C:31]([CH:33]3[CH2:35][CH2:34]3)[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]([CH3:36])[N:30]=[C:31]([CH:33]4[CH2:34][CH2:35]4)[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 69361078phenyl (3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)carbamate

Product 1

HCID 101272591-{(S)-3-[3-(4-Chloro-phenoxy)-azetidin-1-yl]-1-hydroxymethyl-propyl}-3-(5-cyclopropyl-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 (0.158 g, 0.58 mmol) and (5-Cyclopropyl-2-methyl-2H-pyrazol-3-yl)-carbamic acid phenyl ester (0.150 g, 0.58 mmol) in DMSO (3 ml) is stirred at ambient temperature for 6 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 10:90 methanol/dichloromethane) to afford 1-{(S)-3-[3-(4-Chloro-phenoxy)-azetidin-1-yl]-1-hydroxymethyl-propyl}-3-(5-cyclopropyl-2-methyl-2H-pyrazol-3-yl)-urea. [M+H] 434.33.

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 10:90 methanol/dichloromethane)

Sources & evidence

ORD record
ord-e539f2f9add4400e9b12897677f0a750
Source dataset
uspto-grants-2007_10
Patent number
US07288537B2

Reaction notes

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