HCID 86649074, compound → 3-amino-8-(2-oxopyrrolidin-1-yl)-1-(thiophen-3-ylmethyl)-3,4-dihydroquinolin-2(1H)-one

HRID 1887730Notes

Reaction equation

HRID 1887730 reaction equation
C([C@H]([C@@H](C(O)=O)O)O)(O)=O.[NH2:11][CH:12]1[CH2:21][C:20]2[C:15](=[C:16]([N:22]3[CH2:26][CH2:25][CH2:24][C:23]3=[O:27])[CH:17]=[CH:18][CH:19]=2)[N:14]([CH2:28][C:29]2[CH:33]=[CH:32][S:31][CH:30]=2)[C:13]1=[O:34]>C(Cl)(Cl)Cl>[NH2:11][CH:12]1[CH2:21][C:20]2[C:15](=[C:16]([N:22]3[CH2:26][CH2:25][CH2:24][C:23]3=[O:27])[CH:17]=[CH:18][CH:19]=2)[N:14]([CH2:28][C:29]2[CH:33]=[CH:32][S:31][CH:30]=2)[C:13]1=[O:34]

Participants

3

Reactant 1

HCID 86649074HCID 86649074, compound

Product 1

HCID 596203303-amino-8-(2-oxopyrrolidin-1-yl)-1-(thiophen-3-ylmethyl)-3,4-dihydroquinolin-2(1H)-oneYield 86.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3-Amino-8-(2-oxopyrrolidin-1-yl)-1-(thiophen-3-ylmethyl)-3,4-dihydroquinolin-2(1H)-one D-(−)-tartrate (254 g) was suspended in chloroform (1.3 L), and the suspension was extracted with saturated aqueous sodium bicarbonate solution (1.3 L). The organic layers were combined, and the combined organic layer was dried over sodium sulfate. The solvent was evaporated, and ethyl acetate was added to the thus-recovered residue. The precipitates were recovered through filtration and dried, whereby the title compound (153 g) was yielded.

Workup

  1. extractionthe suspension was extracted with saturated aqueous sodium bicarbonate solution (1.3 L)
  2. dry with materialthe combined organic layer was dried over sodium sulfate
  3. customThe solvent was evaporated
  4. additionethyl acetate was added to the thus-recovered residue
  5. filtrationThe precipitates were recovered through filtration
  6. customdried

Sources & evidence

ORD record
ord-6ce95a4621b740ddb3588f62a0d0a622
Source dataset
uspto-grants-2013_08
Patent number
US08501772B2

Reaction notes

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