Picolinic acid → HCID 178503506, compound

HRID 2114562Notes

Reaction equation

HRID 2114562 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([OH:9])=O.[Cl:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[C:25]2[C:20](=[N:21][C:22]([S:27][CH3:28])=[N:23][C:24]=2[NH2:26])[NH:19][N:18]=1.C(NC(C)C)(C)C>S(Cl)(Cl)=O.O1CCCC1>[Cl:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[C:25]2[C:20](=[N:21][C:22]([S:27][CH3:28])=[N:23][C:24]=2[NH:26][C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[O:9])[NH:19][N:18]=1

Participants

6

Reactant 3

HCID 1018Picolinic acidHCID 7912DiisopropylamineHCID 178503484HCID 178503484, compound

Product 1

HCID 178503506HCID 178503506, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 24386Thionyl ChlorideSolvent

Procedure

Pyridine-2-carboxylic acid (78 mg, 0.64 mmol) was placed in 5 ml thionyl chloride and refluxed for 3 hours. Excess thionyl chloride was then removed in vacuo and the crude acid chloride was suspended in 2 ml anhydrous tetrahydrofuran. The solution of acid chloride was added to a mixture of 3-(2-chloro-phenyl)-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine (190 mg, 0.64 mmol) and diisopropylamine (247 mg, 1.92 mmol) in 6 ml anhydrous tetrahydrofuran. The reaction mixture was refluxed for 15 h. After cooling to room temperature the resulting mixture was partition between 60 ml ethylacetate and 15 ml brine. The organic layer was washed 3 times with 3N HCl, next with saturated sodium bicarbonate solution and brine. After drying with sodium sulfate and solvent evaporation in vacuo, 140 mg of pyridine-2-carboxylic acid [3-(2-chloro-phenyl)-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl]-amide, MS: 397.1 (M+H), was obtained.

Workup

  1. temperaturerefluxed for 3 hours
  2. customExcess thionyl chloride was then removed in vacuo
  3. temperatureThe reaction mixture was refluxed for 15 h
  4. customwas partition between 60 ml ethylacetate and 15 ml brine
  5. washThe organic layer was washed 3 times with 3N HCl
  6. dry with materialAfter drying with sodium sulfate and solvent evaporation in vacuo, 140 mg of pyridine-2-carboxylic acid [3-(2-chloro-phenyl)-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl]-amide, MS
  7. custom397.1 (M+H), was obtained

Sources & evidence

ORD record
ord-04f4c019298b4c90998e565f818e0536
Source dataset
uspto-grants-2008_10
Patent number
US07435731B2

Reaction notes

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