Water → HCID 23144689, compound

HRID 337401Notes

Reaction equation

HRID 337401 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:7]=[C:8]([NH:17][C:18]([CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[O:19])[S:9][C:10]=1[C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1.Cl[C:27]1[CH:32]=[CH:31][C:30]([C:33]#[N:34])=[CH:29][N:28]=1.C(=O)([O-])[O-].[K+].[K+].O>CN1C(=O)CCC1>[C:33]([C:30]1[CH:31]=[CH:32][C:27]([N:23]2[CH2:24][CH2:25][CH:20]([C:18]([NH:17][C:8]3[S:9][C:10]([C:11]4[CH:12]=[CH:13][N:14]=[CH:15][CH:16]=4)=[C:6]([C:2]4[O:1][CH:5]=[CH:4][CH:3]=4)[N:7]=3)=[O:19])[CH2:21][CH2:22]2)=[N:28][CH:29]=1)#[N:34]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 51520946-Chloro-3-pyridinecarbonitrileHCID 23144550HCID 23144550, compound

Product 1

HCID 23144689HCID 23144689, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Compound 15 (177 mg, 0.50 mmol), 2-chloro-5-cyanopyridine (104 mg, 0.75 mmol) and potassium carbonate (207 mg, 1.50 mmol) were dissolved in NMP (4 mL), followed by stirring overnight under heating and reflux. The reaction mixture was allowed to cool down to room temperature, then poured into water, and the deposited precipitate was collected by filtration. The resulting precipitate was purified through silica gel column chromatography (chloroform:methanol=17:3) to afford the entitled Compound 16 (114 mg, 50%).

Workup

  1. temperatureunder heating
  2. temperaturereflux
  3. filtrationthe deposited precipitate was collected by filtration
  4. customThe resulting precipitate was purified through silica gel column chromatography (chloroform:methanol=17:3)

Sources & evidence

ORD record
ord-b08241c4f5294a0dbfad45fb21d51e0b
Source dataset
uspto-grants-2014_11
Patent number
US08889718B2

Reaction notes

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