Pyridine → HCID 117737288, compound

HRID 1504553Notes

Reaction equation

HRID 1504553 reaction equation
[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([N:9]2[C:18]3[C:13](=[CH:14][C:15]([S:19](Cl)(=[O:21])=[O:20])=[CH:16][CH:17]=3)[N:12]=[CH:11][C:10]2=[O:23])=[C:4]([O:24][CH3:25])[CH:3]=1.ClCCl.[N:29]1[CH:34]=[CH:33][CH:32]=[C:31]([NH2:35])[N:30]=1.N1C=CC=CC=1>CO.CCOC(C)=O>[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([N:9]2[C:18]3[C:13](=[CH:14][C:15]([S:19]([NH:35][C:31]4[N:30]=[N:29][CH:34]=[CH:33][CH:32]=4)(=[O:21])=[O:20])=[CH:16][CH:17]=3)[N:12]=[CH:11][C:10]2=[O:23])=[C:4]([O:24][CH3:25])[CH:3]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 230373AminopyridazineHCID 117737197HCID 117737197, compound

Product 1

HCID 117737288HCID 117737288, compoundYield 22.2%

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

A RBF was charged with 1-(4-bromo-5-fluoro-2-methoxyphenyl)-2-oxo-1,2-dihydroquinoxaline-6-sulfonyl chloride (527.2 mg, 1.060 mmol), dichloromethane (1767 μl), and pyridazin-3-amine (151 mg, 1.590 mmol) to give a thick suspension. Pyridine (3533 μl) was added relatively quickly, and the mixture was stirred overnight. In the morning, the mixture was concentrated in vacuo, then taken up in 2N aq. HCl and MeOH/EtOAc. A solid formed that was slowly dissolved in the MeOH/EtOAc by repeated exposure. The layers were separated, and the aq. layer was extracted with MeOH/EtOAc (2×). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. The residue was purified by chromatography on silica gel (50-g SNAP Ultra column, 0-50% 3:1 EtOAc/EtOH in heptane with 10% DCM). The main peak was collected with a slightly lower-Rf peak to give 1-(4-bromo-5-fluoro-2-methoxyphenyl)-2-oxo-N-(pyridazin-3-yl)-1,2-dihydroquinoxaline-6-sulfonamide (119 mg, 0.235 mmol, 22.18% yield) as a yellow solid. m/z (ESI) 506.0 (M+H)+.

Workup

  1. customto give a thick suspension
  2. concentrationIn the morning, the mixture was concentrated in vacuo
  3. customA solid formed that
  4. customThe layers were separated
  5. extractionthe aq. layer was extracted with MeOH/EtOAc (2×)
  6. dry with materialThe combined organic extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by chromatography on silica gel (50-g SNAP Ultra column, 0-50% 3:1 EtOAc/EtOH in heptane with 10% DCM)
  10. customThe main peak was collected with a slightly lower-Rf peak

Sources & evidence

ORD record
ord-edd7c49eef2a4a23bdea0e28a2abcfc3
Source dataset
uspto-grants-2015_12
Patent number
US09212182B2

Reaction notes

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