Pyridine → HCID 68470577, compound

HRID 387651Notes

Reaction equation

HRID 387651 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:20]([O:22][CH3:23])=[O:21])[C:5]2[CH2:6][CH2:7][N:8]([CH:13]([CH2:17][CH2:18][CH3:19])[CH2:14][CH2:15][CH3:16])[C:9](=[O:12])[C:10]=2[CH:11]=1.N1C=CC=CC=1.[CH3:30][S:31](Cl)(=[O:33])=[O:32].C(=O)([O-])O.[Na+]>ClCCl.O>[CH3:30][S:31]([NH:1][C:2]1[CH:3]=[C:4]([C:20]([O:22][CH3:23])=[O:21])[C:5]2[CH2:6][CH2:7][N:8]([CH:13]([CH2:17][CH2:18][CH3:19])[CH2:14][CH2:15][CH3:16])[C:9](=[O:12])[C:10]=2[CH:11]=1)(=[O:33])=[O:32]

Participants

7

Reactant 4

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 68472645HCID 68472645, compound

Product 1

HCID 68470577HCID 68470577, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

0.5 g of methyl 7-amino-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate is dissolved under an inert atmosphere in 5 cm3 of dichloromethane at a temperature close to 20° C. 0.142 cm3 of pyridine is poured into the reaction mixture which is then cooled to a temperature close to 5° C. 0.122 cm3 of methanesulfonyl chloride is introduced over 30 min. The stirring is continued for 20 h while gradually allowing it to climb back up to a temperature close to 20° C. 20 cm3 of a saturated aqueous solution of sodium hydrogen carbonate and 5 cm3 of water are added to the reaction mixture. Stirring is continued for 1 h at a temperature close to 20° C. The aqueous phase is extracted with 10 cm3 of dichloromethane. After decanting, the organic phase is dried over magnesium sulfate, filtered then concentrated using a rotary evaporator under reduced pressure (5 kPa). The crude product obtained is purified by trituration in 10 cm3 of hot diisopropyl ether. After filtering at a temperature close to 20° C., washing with 2 lots of 5 cm3 of diisopropyl ether and drying under vacuum, 0.6 g of methyl 7-[(methylsulfonyl)amino]-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate is obtained in the form of pink crystals.

Workup

  1. customclose to 20° C
  2. temperatureis then cooled to a temperature
  3. customclose to 5° C
  4. customclose to 20° C
  5. waitis continued for 1 h at a temperature
  6. customclose to 20° C
  7. extractionThe aqueous phase is extracted with 10 cm3 of dichloromethane
  8. customAfter decanting
  9. dry with materialthe organic phase is dried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationthen concentrated
  12. customa rotary evaporator under reduced pressure (5 kPa)
  13. customThe crude product obtained
  14. customis purified by trituration in 10 cm3 of hot diisopropyl ether
  15. filtrationAfter filtering at a temperature
  16. customclose to 20° C.
  17. washwashing with 2 lots of 5 cm3 of diisopropyl ether
  18. customdrying under vacuum

Sources & evidence

ORD record
ord-ac5f2fbc411d4148a50007b8b3bfb1ed
Source dataset
uspto-grants-2013_02
Patent number
US08372864B2

Reaction notes

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