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

반응식

HRID 1182153 반응식
[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

참가 물질

4

반응물 2

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

생성물 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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bde66ebe4c6e4280912343d9ba9d4257
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07288537B2

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