Pyridine → HCID 44526983, compound

HRID 1625960Notes

Reaction equation

HRID 1625960 reaction equation
[NH2:1][C:2]1[C:7]([S:8](Cl)(=[O:10])=[O:9])=[CH:6][C:5]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]=[CH:17][CH:16]=[C:15]3[C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)=[CH:4][N:3]=1.O1CCOCC1.[NH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1.N1C=CC=CC=1>ClS(O)(=O)=O>[N:34]1([S:8]([C:7]2[C:2]([NH2:1])=[N:3][CH:4]=[C:5]([C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[CH:17][CH:16]=[C:15]4[C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)[CH:6]=2)(=[O:10])=[O:9])[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8082PiperidineHCID 312751,4-DioxaneHCID 86625113HCID 86625113, compound

Product 1

HCID 44526983HCID 44526983, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 24638Chlorosulfonic acidSolvent

Procedure

To a cold (5° C.) solution of the 0.456 M solution of 2-amino-5-[4-(4-pyridinyl)-6-quinolinyl]-3-pyridinesulfonyl chloride (2 mL, 0.912 mmol) in chlorosulfonic acid from above was added anhydrous dioxane (1 mL) and piperidine (1.8 mL, 18.24 mmol). After 30 minutes of stirring, pyridine (1 mL, 12.3 mmol) was added and the reaction mixture stirred for an additional hour at room temperature. The reaction mixture was concentrated in vacuo, the residue dissolved in CH2Cl2 and the pH adjusted to 14 using 6 N NaOH (aq). The solution was extracted with CH2Cl2 (×4) and the combined organic layers dried (Na2SO4), filtered and concentrated in vacuo. The resulting residue was purified twice by silica gel chromatography (0-5% MeOH in EtOAC) to give the title compound as a pale yellow solid (269 mg, 66% yield). MS(ES)+ m/e 446.3 [M+H]+.

Workup

  1. stirringthe reaction mixture stirred for an additional hour at room temperature
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionthe residue dissolved in CH2Cl2
  4. extractionThe solution was extracted with CH2Cl2 (×4)
  5. dry with materialthe combined organic layers dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue was purified twice by silica gel chromatography (0-5% MeOH in EtOAC)

Sources & evidence

ORD record
ord-e5b0e61f34f9472ba9f1b51fec9b4447
Source dataset
uspto-grants-2014_07
Patent number
US08785433B2

Reaction notes

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