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Triethylamine → 2-chloro-N-[1-(2-hydroxyethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamide

HRID 1247499
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HRID 1247499 반응식
C(N(CC)CC)C.ClC(OCC)=O.[C:14]([CH2:17][N:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21][CH:20]([NH:28][C:29]([C:31]2[NH:35][C:34]3[S:36][C:37]([Cl:39])=[CH:38][C:33]=3[CH:32]=2)=[O:30])[C:19]1=[O:40])(O)=[O:15].[Li+].[BH4-]>C1COCC1>[Cl:39][C:37]1[S:36][C:34]2[NH:35][C:31]([C:29]([NH:28][CH:20]3[CH2:21][C:22]4[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=4)[N:18]([CH2:17][CH2:14][OH:15])[C:19]3=[O:40])=[O:30])=[CH:32][C:33]=2[CH:38]=1
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참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 4148881Lithium borohydrideHCID 10319016N-[1-(Carboxymethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-2-chloro-6H-thieno[2,3-b]pyrrole-5-carboxamide

생성물 1

HCID 104304502-chloro-N-[1-(2-hydroxyethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamide수율 88%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Triethylamine (0.76 mL, 5.47 mmol) then ethyl chloroformate (0.52 mL, 5.47 mmol) were added to N-[1-(carboxymethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-2-chloro-6H-thieno[2,3-b]pyrrole-5-carboxamide (Example 2; 2.0 g, 4.97 mmol) in anhydrous THF (40 mL) at 0° C. followed by stirring for 1 h. LiBH4 (2.0 M in THF, 3.1 mL, 6.21 mmol) was added slowly and the mixture stirred for a further 30 min. The reaction was carefully quenched with 1M HCl (200 mL) and EtOAc (400 mL) and the organic layer was further washed with sat. aqueous NaHCO3 (100 mL), brine (100 mL), dried (MgSO4), filtered and evaporated. The residue was triturated with refluxing Et2O (30 mL) and after cooling the solid was filtered and dried to afford the title compound (1.70 g, 88%) as a white solid.

후처리

  1. stirringthe mixture stirred for a further 30 min
  2. customThe reaction was carefully quenched with 1M HCl (200 mL) and EtOAc (400 mL)
  3. washthe organic layer was further washed with sat. aqueous NaHCO3 (100 mL), brine (100 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was triturated with refluxing Et2O (30 mL)
  8. temperatureafter cooling the solid
  9. filtrationwas filtered
  10. customdried

출처 및 근거

ORD 기록
ord-faac4678271e4f5581e5883b95b6af82
출처 데이터셋
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07129249B2

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