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

HRID 1182153

反応式

HRID 1182153 の反応式
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][CH:7]2[CH2:10][N:9]([CH2:11][CH2:12][C@H:13]([NH2:15])[CH3:14])[CH2:8]2)=[CH:4][CH:3]=1.C1([O:24][C:25](=O)[NH:26][C:27]2[S:28][C:29]([CH2:32][CH3:33])=[N:30][N:31]=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:15][C:25]([NH:26][C:27]3[S:28][C:29]([CH2:32][CH3:33])=[N:30][N:31]=3)=[O:24])[CH3:14])[CH2:8]2)=[CH:16][CH:17]=1

参加物

4

反応物 2

HCID 66876196Phenyl 5-ethyl-1,3,4-thiadiazol-2-ylcarbamateHCID 69409912(R)-3-[3-(4-chloro-phenoxy)-azetidin-1-yl]-1-methyl-propylamine

生成物 1

HCID 101268841-{(R)-3-[3-(4-Chloro-phenoxy)-azetidin-1-yl]-1-methyl-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 (R)-3-[3-(4-chloro-phenoxy)-azetidin-1-yl]-1-methyl-propylamine (0.145 mg, 0.569 mmol) and (5-ethyl-[1,3,4]thiadiazol-2-yl)-carbamic acid phenyl ester (0.142 mg, 0.569 mmol) in DMSO is stirred at room temperature for 4 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 recrystallised from hot ethylacetate to afford 1-{(R)-3-[3-(4-Chloro-phenoxy)-azetidin-1-yl]-1-methyl-propyl}-3-(5-ethyl-[1,3,4]thiadiazol-2-yl)-urea. [M+H] 410.14.

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 recrystallised from hot ethylacetate

出典と根拠

ORDレコード
ord-bde66ebe4c6e4280912343d9ba9d4257
出典データセット
uspto-grants-2007_10
特許番号
US07288537B2

関連ノート

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