Sodium Thiosulfate → 7-[(5-Benzyloxy-pyridin-2-yl)-pyridin-2-yl-amino]heptanoic acid ethyl ester

HRID 404153Notes

Reaction equation

HRID 404153 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:12]=[CH:13][C:14]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)=[N:15][CH:16]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32].[O-]S([O-])(=S)=O.[Na+].[Na+]>CN(C=O)C.CCOC(C)=O>[CH2:34]([O:33][C:31](=[O:32])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][N:17]([C:14]1[CH:13]=[CH:12][C:11]([O:10][CH2:3][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)=[CH:16][N:15]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)[CH3:35]

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 24758Sodium hydrideHCID 122490Ethyl 7-bromoheptanoateHCID 86660143(5-Benzyloxy-pyridin-2-yl)-pyridin-2-yl-amine

Product 1

HCID 585450367-[(5-Benzyloxy-pyridin-2-yl)-pyridin-2-yl-amino]heptanoic acid ethyl esterYield 56.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

NaH (48 mg, 1.26 6 mmol) was added to II (350 mg, 1.26 mmol) in DMF (6 mL) at rt. After 10 min, KI (314 mg, 1.89 mmol) and ethyl 7-bromoheptanoate (0.370 mL, 1.89 mmol) were added. The reaction mixture was stirred at 90° C. for 18 h30 after which 0.1 M Na2S2O3 (50 mL) and EtOAc (50 mL) were added, the phases were separated and the aqueous 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 (80:20 then 70:30) to furnish III as a colourless oil (308 mg, 56%).

Workup

  1. additionwere added
  2. customthe phases were separated
  3. extractionthe aqueous 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 (80:20

Sources & evidence

ORD record
ord-3561d85bc5bb411b8fdf5851c8dec94d
Source dataset
uspto-grants-2014_06
Patent number
US08748458B2

Reaction notes

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