Water → 1-(5-(1-cyanoethoxy)-2,3',5'-trifluoro-[1,1'-biphenyl]-4-yl)-N-(isoxazol-3-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide

HRID 1504378Notes

Reaction equation

HRID 1504378 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([N:6](CC2C=CC(OC)=CC=2)[S:7]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]([C:20]2[C:25]([OH:26])=[CH:24][C:23]([C:27]4[CH:32]=[C:31]([F:33])[CH:30]=[C:29]([F:34])[CH:28]=4)=[C:22]([F:35])[CH:21]=2)[C:15](=[O:36])[CH:14]=[CH:13]3)(=[O:9])=[O:8])=[N:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH:53]([CH3:56])[C:54]#[N:55].O>CN(C=O)C>[C:54]([CH:53]([O:26][C:25]1[C:20]([N:16]2[C:17]3[C:12](=[CH:11][C:10]([S:7]([NH:6][C:3]4[CH:4]=[CH:5][O:1][N:2]=4)(=[O:8])=[O:9])=[CH:19][CH:18]=3)[CH:13]=[CH:14][C:15]2=[O:36])=[CH:21][C:22]([F:35])=[C:23]([C:27]2[CH:32]=[C:31]([F:33])[CH:30]=[C:29]([F:34])[CH:28]=2)[CH:24]=1)[CH3:56])#[N:55]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1405382-BromopropionitrileHCID 117737313N-(isoxazol-3-yl)-N-(4-methoxybenzyl)-2-oxo-1-(2,3',5'-trifluoro-5-hydroxy-[1,1'-biphenyl]-4-yl)-1,2-dihydroquinoline-6-sulfonamide

Product 1

HCID 1177368451-(5-(1-cyanoethoxy)-2,3',5'-trifluoro-[1,1'-biphenyl]-4-yl)-N-(isoxazol-3-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(isoxazol-3-yl)-N-(4-methoxybenzyl)-2-oxo-1-(2,3′,5′-trifluoro-5-hydroxy-[1,1′-biphenyl]-4-yl)-1,2-dihydroquinoline-6-sulfonamide (0.066 g, 0.104 mmol) in DMF (0.208 ml) at room temperature was added potassium carbonate (0.016 g, 0.115 mmol) followed by 2-bromopropanenitrile (0.014 ml, 0.156 mmol). The reaction mixture was stirred 16 hr. The resulting mixture was transferred to a sep.funnel containing water and the aqueous layer was washed 3× with DCM. The organic layers were combined, dried with MgSO4, filtered and concentrated to an oil. The crude material was taken onward to the next step without further purification, assuming quantitative yield. m/z (ESI) 687.1 (M+H)+.

Workup

  1. washthe aqueous layer was washed 3× with DCM
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to an oil
  5. customThe crude material was taken onward to the next step without further purification

Sources & evidence

ORD record
ord-dc833e7e7ff84804a006945c0c65e23a
Source dataset
uspto-grants-2015_12
Patent number
US09212182B2

Reaction notes

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