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

HRID 523895Notes

Reaction equation

HRID 523895 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-c24b48f5ff2f439ba98f8b2199042960
Source dataset
uspto-grants-2016_05
Patent number
US09340503B2

Reaction notes

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