Dimethyl Sulfide → HCID 21912234, compound

HRID 1760690Notes

Reaction equation

HRID 1760690 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[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=2[Cl:24])[N:10]=[C:9]([CH3:25])[CH:8]=1)[CH2:4][CH3:5])[CH3:2].CSC>C1COCC1>[Cl:24][C:18]1[CH:19]=[C:20]([Cl:23])[CH:21]=[CH:22][C:17]=1[NH:16][C:11]1[C:12]([CH2:13][OH:14])=[C:7]([O:6][CH:3]([CH2:4][CH3:5])[CH2:1][CH3:2])[CH:8]=[C:9]([CH3:25])[N:10]=1

Participants

4

Reactant 2

HCID 1068Dimethyl SulfideHCID 21912362HCID 21912362, compound

Product 1

HCID 21912234HCID 21912234, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(1-ethyl-propoxy)-6-methyl-2-(2,4-dichloro-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 min, adjusted pH to 7.5-8.5, then extracted with ethyl acetate. The organic layer was separated, dried and concentrated to give a golden oil. After silica gel column chromatography, the Ute compound was obtained as a golden oil. 1H NMR(CDCl3) d 8.44(d,1H), 8.18(s,1H), 7.32(d,1H), 7.179d,1H), 6.28(s,1H), 4.82(s,2H), 4.21(m,1H), 2.42(s,3H), 1.6-1.8(m,4H), 0.94(t,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 golden oil
  9. customAfter silica gel column chromatography, the Ute compound was obtained as a golden oil

Sources & evidence

ORD record
ord-279c108f27744729b5bc66be61fc4005
Source dataset
uspto-grants-2005_01
Patent number
US06844351B1

Reaction notes

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