Triethylamine → 5-Chloro-N-[1-(2-hydroxyethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-1H-indole-2-carboxamide

HRID 1376145ノート

反応式

HRID 1376145 の反応式
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:32][C:33]3[C:38]([CH:39]=2)=[CH:37][C:36]([Cl:40])=[CH:35][CH:34]=3)=[O:30])[C:19]1=[O:41])(O)=[O:15].[Li+].[BH4-]>C1COCC1>[Cl:40][C:36]1[CH:37]=[C:38]2[C:33](=[CH:34][CH:35]=1)[NH:32][C:31]([C:29]([NH:28][CH:20]1[CH2:21][C:22]3[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:18]([CH2:17][CH2:14][OH:15])[C:19]1=[O:41])=[O:30])=[CH:39]2

参加物

6

反応物 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 4148881Lithium borohydrideHCID 101266823,4-dihydro-2-quinolone (DHQ) derivative, 10

生成物 1

HCID 102872925-Chloro-N-[1-(2-hydroxyethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-1H-indole-2-carboxamide収率 77%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Triethylamine (0.168 mL, 1.21 mmol) then ethyl chloroformate (0.115 mL, 1.21 mmol) were added to N-[1-(carboxymethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-5-chloroindole-2-carboxamide (Example 2, 437 mg, 1.10 mmol) in anhydrous THF (10 mL) at 0° C. followed by stirring for 1 h. LiBH4 (2.0 M in THF, 0.69 mL, 1.37 mmol) was added slowly and the mixture stirred for a further 30 min. The reaction was carefully quenched with 1M HCl (50 mL) and EtOAc (100 mL) and the organic layer was further washed with sat. aqueous NaHCO3 (30 mL), brine (30 mL), dried (MgSO4), filtered and evaporated. The residue was triturated with refluxing Et2O (10 mL) and after cooling the solid was filtered and dried to afford the title compound (325 mg, 77%) a white solid.

後処理

  1. stirringthe mixture stirred for a further 30 min
  2. customThe reaction was carefully quenched with 1M HCl (50 mL) and EtOAc (100 mL)
  3. washthe organic layer was further washed with sat. aqueous NaHCO3 (30 mL), brine (30 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was triturated with refluxing Et2O (10 mL)
  8. temperatureafter cooling the solid
  9. filtrationwas filtered
  10. customdried

出典と根拠

ORDレコード
ord-e23cc67a4a4d4108aaaf9b91bc9a97f6
出典データセット
uspto-grants-2007_01
特許番号
US07169927B2

反応ノート

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