Methanol → HCID 59486218, compound

HRID 1949176Notes

Reaction equation

HRID 1949176 reaction equation
[Na].Cl[C:3]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([F:16])([F:15])[F:14])=[CH:10][CH:11]=2)[N:6]=[C:5]([S:17][CH2:18][CH3:19])[C:4]=1[C:20]([NH:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=1)=[O:21].CCCCCC.[CH3:37][OH:38]>>[CH2:18]([S:17][C:5]1[C:4]([C:20]([NH:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=2)=[O:21])=[C:3]([O:38][CH3:37])[C:12]2[C:7](=[CH:8][C:9]([C:13]([F:16])([F:15])[F:14])=[CH:10][CH:11]=2)[N:6]=1)[CH3:19]

Participants

5

Reactant 4

HCID 887Methanol2×HCID 8058HexaneHCID 5360545Sodium2×HCID 59486210HCID 59486210, compound

Product 1

HCID 59486218HCID 59486218, compoundYield 38%

Conditions

Temperature
60 °C

Procedure

20 mg (0.95 mmol) sodium were added to methanol (6 ml) at RT. Once the sodium had completely dissolved, a solution of 210 mg (0.47 mmol) 4-chloro-2-ethylsulfanyl-N-[(3-fluorophenyl)-methyl]-7-(trifluoromethyl)-quinoline-3-carboxamide (example 122) in MeOH (2 ml) was added at RT. The mixture was then heated for 30 min at 60° C. Then the mixture was concentrated to small volume under vacuum and the residue was taken up with water and extracted with EE. The organic phase was washed with water and brine, dried over Na2SO4, filtered and concentrated to small volume under vacuum. Column chromatography (hexane/EE 9:1) of the residue yielded 80 mg (0.18 mmol, 38%) 2-ethylsulfanyl-N-[(3-fluorophenyl)-methyl]-4-methoxy-7-(trifluoromethyl)-quinoline-3-carboxamide. MS: m/z 439.1 [M+H]+.

Workup

  1. concentrationThen the mixture was concentrated to small volume under vacuum
  2. extractionextracted with EE
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to small volume under vacuum

Sources & evidence

ORD record
ord-ec91a1ecf3604583a9b33559c52801bb
Source dataset
uspto-grants-2013_03
Patent number
US08399673B2

Reaction notes

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