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

反応式

HRID 1182152 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-ada1071260eb4f528c5b64d0239dc748
出典データセット
uspto-grants-2007_10
特許番号
US07288537B2

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