Hydrochloric Acid → HCID 86606164, compound

HRID 269791Notes

Reaction equation

HRID 269791 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:8]([Li])[CH2:9][CH2:10]C.[Cl:13][C:14]1[N:19]=[C:18](S(C)(=O)=O)[N:17]=[C:16]([NH:24]C(C)C)[C:15]=1[C:28]1[C:33]([F:34])=[CH:32][CH:31]=[CH:30][C:29]=1[Cl:35].Cl>O1CCCC1>[Cl:13][C:14]1[N:19]([CH:9]([CH3:10])[CH3:8])[CH:18]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:17]=[C:16]([NH2:24])[C:15]=1[C:28]1[C:33]([F:34])=[CH:32][CH:31]=[CH:30][C:29]=1[Cl:35]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 86606165HCID 86606165, compoundHCID 178418339Butyllithium

Product 1

HCID 86606164HCID 86606164, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

At −70° C., 0.62 g (6.6 mmol) of aniline was added to a suspension of 2.9 g of butyllithium (15% solution in hexane) in 15 ml of tetrahydrofuran [THF], and the mixture was then stirred at −70° C. for 1 hour. 1.0 g (2.64 mmol) of [6-chloro-5-(2-chloro-6-fluorophenyl)-2-methanesulfonylpyrimidin-4-yl]isopropylamine (abbr. sulfone 3) was added, and the mixture was then warmed to 20-25° C. The reaction mixture was poured into ice-water and acidified with hydrochloric acid. The mixture was extracted with 2×40 ml of MTBE, and the combined organic phases gave, after drying and distillative removal of the solvent, 1.0 g of the title compound.

Workup

  1. temperaturethe mixture was then warmed to 20-25° C
  2. extractionThe mixture was extracted with 2×40 ml of MTBE
  3. customthe combined organic phases gave
  4. customafter drying
  5. customdistillative removal of the solvent, 1.0 g of the title compound

Sources & evidence

ORD record
ord-6fa615061bfa4860bc5558c4a5d54310
Source dataset
uspto-grants-2008_11
Patent number
US07449471B2

Reaction notes

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