Hydrochloric Acid → HCID 131727492, compound

HRID 1986106Notes

Reaction equation

HRID 1986106 reaction equation
[C:1]([C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18]3[C:23]([C:24]([O-])=[O:25])=[CH:22][N:21]=[C:20]([S:27][CH3:28])[N:19]=3)=[CH:13][C:12]=2[F:29])[CH:7]=[CH:6][N:5]=1)(=[O:3])[NH2:2].[Na+].S(Cl)([Cl:33])=O.[F:35][C:36]1[CH:42]=[C:41]([F:43])[CH:40]=[CH:39][C:37]=1[NH2:38].Cl>C1C=CC=CC=1.O>[ClH:33].[C:1]([C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18]3[C:23]([C:24]([NH:38][C:37]4[CH:39]=[CH:40][C:41]([F:43])=[CH:42][C:36]=4[F:35])=[O:25])=[CH:22][N:21]=[C:20]([S:27][CH3:28])[N:19]=3)=[CH:13][C:12]=2[F:29])[CH:7]=[CH:6][N:5]=1)(=[O:3])[NH2:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 97092,4-DifluoroanilineHCID 24386Thionyl ChlorideHCID 57721338HCID 57721338, compound

Product 1

HCID 131727492HCID 131727492, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

To a suspension of sodium 4-(4-(2-carbamoylpyridin-4-yloxy)-3-fluorophenylamino)-2-(methylthio)pyrimidine-5-carboxylate (2.94 g, 6.72 mmol) in benzene (75 mL) was added thionyl chloride (4.9 mL, 62 mmol) and the solution was refluxed for 3 h. The reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was treated with benzene and again concentrated in vacuo to remove the residual thionyl chloride. The resulting solid was taken up in THF (75 mL) and was treated with 2,4-difluoroaniline (2.6 g, 20.2 mmol). After stirring overnight the mixture was acidified with dilute aqueous HCl, was diluted with water (400 mL), and filtered. The resulting solid was purified by repeated trituration with methanol or ethyl acetate to give the amide (1.69 g, 45%) as a solid. MS(ESI+) m/z 527 (M+H)+.

Workup

  1. temperaturethe solution was refluxed for 3 h
  2. concentrationconcentrated in vacuo
  3. additionThe residue was treated with benzene
  4. concentrationagain concentrated in vacuo
  5. customto remove the residual thionyl chloride
  6. filtrationfiltered
  7. customThe resulting solid was purified

Sources & evidence

ORD record
ord-39efec6ce8734b36a0438acebe50dd27
Source dataset
uspto-grants-2009_06
Patent number
US07547782B2

Reaction notes

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