[(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 1178427ノート

反応式

HRID 1178427 の反応式
[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

参加物

3

反応物 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

生成物 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-carboxamide収率 87%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-20975203eb3e4781b6a7fea4352eb469
出典データセット
uspto-grants-2007_10
特許番号
US07276517B2

反応ノート

読み込み中…