[(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 1247510Notes

Reaction equation

HRID 1247510 reaction equation
[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

Participants

3

Reactant 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

Product 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-carboxamideYield 87%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-0b82fd1174eb448bbf46a6843e94457a
Source dataset
uspto-grants-2006_10
Patent number
US07129249B2

Reaction notes

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