[(Z)-[1-amino-2-[3-[(2-chloro-6H-thieno[2,3-b]pyrrole-5-carbonyl)amino]-2-oxo-3,4-dihydroquinolin-1-yl]ethylidene]amino] ethyl carbonate → 2-Chloro-N-{2-oxo-1-[(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)methyl]-1,2,3,4-tetrahydroquinolin-3-yl}-6H-thieno[2,3-b]pyrrole-5-carboxamide

HRID 1178427노트

반응식

HRID 1178427 반응식
[NH2:1]/[C:2](=[N:27]\[O:28][C:29](OCC)=[O:30])/[CH2:3][N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH:6]([NH:14][C:15]([C:17]2[NH:21][C:20]3[S:22][C:23]([Cl:25])=[CH:24][C:19]=3[CH:18]=2)=[O:16])[C:5]1=[O:26]>O1CCOCC1>[Cl:25][C:23]1[S:22][C:20]2[NH:21][C:17]([C:15]([NH:14][CH:6]3[CH2:7][C:8]4[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=4)[N:4]([CH2:3][C:2]4[NH:1][C:29](=[O:30])[O:28][N:27]=4)[C:5]3=[O:26])=[O:16])=[CH:18][C:19]=2[CH:24]=1

참가 물질

3

반응물 1

HCID 21906825[(Z)-[1-amino-2-[3-[(2-chloro-6H-thieno[2,3-b]pyrrole-5-carbonyl)amino]-2-oxo-3,4-dihydroquinolin-1-yl]ethylidene]amino] ethyl carbonate

생성물 1

HCID 1354575442-Chloro-N-{2-oxo-1-[(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)methyl]-1,2,3,4-tetrahydroquinolin-3-yl}-6H-thieno[2,3-b]pyrrole-5-carboxamide수율 87%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

N-[1-((2Z)-2-Amino-2-{[(ethoxycarbonyl)oxy]imino}ethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-2-chloro-6H-thieno[2,3-b]pyrrole-5-carboxamide (Method 14) was dissolved in 1,4-Dioxane and the solvent distilled off with the oil bath temperature 140° C. This was repeated 4 times. The residual solid was triturated with refluxing Et2O (10 mL) and after cooling filtered, washed with Et2O (10 mL) and hexane (10 mL) to give the title product (184 mg, 87% (2 steps)) as a pale brown solid.

후처리

  1. distillationthe solvent distilled off with the oil bath temperature 140° C
  2. customThe residual solid was triturated with refluxing Et2O (10 mL)
  3. temperatureafter cooling
  4. filtrationfiltered
  5. washwashed with Et2O (10 mL) and hexane (10 mL)

출처 및 근거

ORD 기록
ord-20975203eb3e4781b6a7fea4352eb469
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07276517B2

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