Phenyl 5-ethyl-1,3,4-thiadiazol-2-ylcarbamate → 1-{3-[3-(4-Chloro-benzyl)-azetidin-1-yl]-propyl}-3-(5-ethyl-[1,3,4]thiadiazol-2-yl)-urea

HRID 1182152

Reaction equation

HRID 1182152 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][CH:7]2[CH2:10][N:9]([CH2:11][CH2:12][CH2:13][NH2:14])[CH2:8]2)=[CH:4][CH:3]=1.C1([O:23][C:24](=O)[NH:25][C:26]2[S:27][C:28]([CH2:31][CH3:32])=[N:29][N:30]=2)C=CC=CC=1>CS(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]2[CH2:10][N:9]([CH2:11][CH2:12][CH2:13][NH:14][C:24]([NH:25][C:26]3[S:27][C:28]([CH2:31][CH3:32])=[N:29][N:30]=3)=[O:23])[CH2:8]2)=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 66876196Phenyl 5-ethyl-1,3,4-thiadiazol-2-ylcarbamateHCID 694091233-(3-(4-Chlorobenzyl)azetidin-1-yl)propan-1-amine

Product 1

HCID 101506761-{3-[3-(4-Chloro-benzyl)-azetidin-1-yl]-propyl}-3-(5-ethyl-[1,3,4]thiadiazol-2-yl)-urea

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 3-[3-(4 chloro-benzyl)-azetidin-1-yl]-propylamine (0.100 mg, 0.418 mmol) and (5-ethyl-[1,3,4]thiadiazol-2-yl)-carbamic acid phenyl ester (0.11 mg, 0.439 mmol) in DMSO is stirred at room temperature for 18 hours then partitioned between ethylacetate and water. The organic phase is washed with brine and dried over magnesium sulphate and evaporated. The crude product is purified by flash silica chromatography using 5% methanol in DCM as eluent to afford 1-{3-[3-(4-chloro-benzyl)-azetidin-1-yl]-propyl}-3-(5-ethyl-[1,3,4]thiadiazol-2-yl)-urea. [M+H] 394.1

Workup

  1. customthen partitioned between ethylacetate and water
  2. washThe organic phase is washed with brine
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customThe crude product is purified by flash silica chromatography

Sources & evidence

ORD record
ord-ada1071260eb4f528c5b64d0239dc748
Source dataset
uspto-grants-2007_10
Patent number
US07288537B2

Linked notes

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