Dimethyl Sulfide → HCID 21912053, compound

HRID 1245731Notes

Reaction equation

HRID 1245731 reaction equation
[CH2:1]([CH:3]([O:6][C:7]1[C:12]([C:13](O)=[O:14])=[C:11]([NH:16][C:17]2[C:22]([CH3:23])=[CH:21][C:20]([Cl:24])=[CH:19][C:18]=2[CH3:25])[N:10]=[C:9]([CH3:26])[CH:8]=1)[CH2:4][CH3:5])[CH3:2].CSC>C1COCC1>[Cl:24][C:20]1[CH:19]=[C:18]([CH3:25])[C:17]([NH:16][C:11]2[C:12]([CH2:13][OH:14])=[C:7]([O:6][CH:3]([CH2:1][CH3:2])[CH2:4][CH3:5])[CH:8]=[C:9]([CH3:26])[N:10]=2)=[C:22]([CH3:23])[CH:21]=1

Participants

4

Reactant 2

HCID 1068Dimethyl SulfideHCID 21912446HCID 21912446, compound

Product 1

HCID 21912053HCID 21912053, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(1-ethyl-propoxy)-6-methyl-2-(4-chloro-2,6-dimethyl-phenylamino)-nicotinic acid in dry THF was added BH3.DMS. The resulting mixture was heated at reflux overnight. The mixture was quenched with dilute HCl and stirred for 30 minutes, adjusted pH to 7.5–8.5, then extracted with ethyl acetate. The organic layer was separated, dried and concentrated to give a brown oil. After silica gel column chromatography, the title compound was obtained as a green oil. 1H NMR(CDCl3) d 7.02(s,2H), 6.83(brs,1H), 4.78(s,2H), 4.14(m,1H), 2.2(s,3H), 2.13(s,6H), 1.66(m,4H), 0.93(9t,6H) ppm.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux overnight
  3. customThe mixture was quenched with dilute HCl
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was separated
  6. customdried
  7. concentrationconcentrated
  8. customto give a brown oil

Sources & evidence

ORD record
ord-d40d6eb0ad5344c7ae5463fabbcc0b16
Source dataset
uspto-grants-2006_10
Patent number
US07125880B1

Reaction notes

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