Sodium Thiosulfate → 7-(Pyridin-2-yl-quinolin-2-yl-amino)-heptanoic acid ethyl ester

HRID 404139ノート

反応式

HRID 404139 の反応式
[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1.Br[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28].[O-]S([O-])(=S)=O.[Na+].[Na+]>CN(C=O)C.CCOC(C)=O>[CH2:30]([O:29][C:27](=[O:28])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][N:9]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][N:3]=1)[C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1)[CH3:31]

参加物

7

反応物 4

HCID 24477Sodium ThiosulfateHCID 24758Sodium hydrideHCID 122490Ethyl 7-bromoheptanoateHCID 53401122-Pyridyl-2-quinolylamine

生成物 1

HCID 585450237-(Pyridin-2-yl-quinolin-2-yl-amino)-heptanoic acid ethyl ester収率 55%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

NaH (35 mg, 0.91 mmol) was added to II (344 mg, 0.91 mmol) in DMF (5 mL) at rt. After 10 min, KI (227 mg, 1.37 mmol) and ethyl 7-bromoheptanoate (0.267 mL, 1.37 mmol) were added. The reaction mixture was stirred at 90° C. for 19 h after which 0.1 M Na2S2O3 (50 mL) and EtOAc (50 mL) were added; the phases were then separated and the aqueous phase extracted with EtOAc (2×25 mL). The organic phases were combined then dried over MgSO4, filtered, and subsequently evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography, eluting with hexane/EtOAc (90:10 to 85:15), to furnish III as a colourless oil (189 mg, 55%).

後処理

  1. additionwere added
  2. customthe phases were then separated
  3. extractionthe aqueous phase extracted with EtOAc (2×25 mL)
  4. dry with materialThe organic phases were combined then dried over MgSO4
  5. filtrationfiltered
  6. customsubsequently evaporated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography
  8. washeluting with hexane/EtOAc (90:10 to 85:15)

出典と根拠

ORDレコード
ord-7e836a4a64ad460e8a34a68a6325da22
出典データセット
uspto-grants-2014_06
特許番号
US08748458B2

反応ノート

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