Pyridine → HCID 67156780, compound

HRID 549285Notes

Reaction equation

HRID 549285 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[Cl:9])[NH2:5].N1C=CC=CC=1.Cl[C:17]1[C:22]2[CH:23]=[C:24]([S:26](Cl)(=[O:28])=[O:27])[S:25][C:21]=2[CH:20]=[CH:19][N:18]=1.[NH:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][S:26]([C:24]2[S:25][C:21]3[CH:20]=[CH:19][N:18]=[C:17]([N:30]4[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]4)[C:22]=3[CH:23]=2)(=[O:28])=[O:27])[CH:6]=[CH:7][C:8]=1[Cl:9]

Participants

7

Reactant 5

HCID 1049PyridineHCID 4837PiperazineHCID 72573,4-DichloroanilineHCID 11430Potassium CarbonateHCID 19350980HCID 19350980, compound

Product 1

HCID 67156780HCID 67156780, compoundYield 2.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

3,4-Dichloroaniline (0.49 mmol), was dissolved in acetonitrile (1 mL) and pyridine (0.440 mL, 4.03 mmol) was added to a solution of 4-chlorothieno[3,2-c]pyridine-2-sulfonyl chloride (0.445 mmol) dissolved in acetonitrile (1 mL). The reaction was shaken for 1 h, controlled with HPLC and the solvent was removed. The crude product was used in the next step without further purification. To the reaction mixture from the previous step, dissolved in DMSO (1 mL), piperazine (15 equiv.) and K2CO3 (1 equiv.) was added. The reaction was stirred at 100° C. for 24 and than concentrated. The product was purified by LC-MS and gave 5.8 mg (2.6%) of the title product. 1H NMR (270 MHz, CH3OH-d4) δ ppm 8.07-8.05 (m, 2H) 7.73 (d, J=6.60 Hz, 1H) 7.46-7.41 (m, 2H) 7.16 (dd, J=8.71, 2.38 Hz, 1H) 3.94-3.90 (m, 4H) 3.92 (m, 4H) 3.53-3.50 (m, 4H); LC-MS 443 (M−H)+; Purity (HPLC) 95%.

Workup

  1. customthe solvent was removed
  2. customThe crude product was used in the next step without further purification
  3. dissolutionTo the reaction mixture from the previous step, dissolved in DMSO (1 mL)
  4. stirringThe reaction was stirred at 100° C. for 24
  5. concentrationthan concentrated
  6. customThe product was purified by LC-MS

Sources & evidence

ORD record
ord-2963661df3884107973e4aa677e86a69
Source dataset
uspto-grants-2011_05
Patent number
US07943639B2

Reaction notes

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