Water → tert-butyl 3-((3',5',6-trifluoro-4-(6-(N-(isoxazol-3-yl)-N-(4-methoxybenzyl)sulfamoyl)-2-oxoquinolin-1(2H)-yl)-[1,1'-biphenyl]-3-yl)oxy)azetidine-1-carboxylate

HRID 1504398Notes

Reaction equation

HRID 1504398 reaction equation
[C:1]([N:8]1[CH2:11][CH:10](I)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[O:13]1[CH:17]=[CH:16][C:15]([N:18]([CH2:49][C:50]2[CH:55]=[CH:54][C:53]([O:56][CH3:57])=[CH:52][CH:51]=2)[S:19]([C:22]2[CH:23]=[C:24]3[C:29](=[CH:30][CH:31]=2)[N:28]([C:32]2[C:37]([OH:38])=[CH:36][C:35]([C:39]4[CH:44]=[C:43]([F:45])[CH:42]=[C:41]([F:46])[CH:40]=4)=[C:34]([F:47])[CH:33]=2)[C:27](=[O:48])[CH:26]=[CH:25]3)(=[O:21])=[O:20])=[N:14]1.C(=O)([O-])[O-].[Cs+].[Cs+].O>C(#N)C>[F:45][C:43]1[CH:44]=[C:39]([C:35]2[C:34]([F:47])=[CH:33][C:32]([N:28]3[C:29]4[C:24](=[CH:23][C:22]([S:19](=[O:21])(=[O:20])[N:18]([C:15]5[CH:16]=[CH:17][O:13][N:14]=5)[CH2:49][C:50]5[CH:51]=[CH:52][C:53]([O:56][CH3:57])=[CH:54][CH:55]=5)=[CH:31][CH:30]=4)[CH:25]=[CH:26][C:27]3=[O:48])=[C:37]([O:38][CH:10]3[CH2:11][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9]3)[CH:36]=2)[CH:40]=[C:41]([F:46])[CH:42]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 11000522Tert-butyl 3-iodoazetidine-1-carboxylateHCID 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 117737258tert-butyl 3-((3',5',6-trifluoro-4-(6-(N-(isoxazol-3-yl)-N-(4-methoxybenzyl)sulfamoyl)-2-oxoquinolin-1(2H)-yl)-[1,1'-biphenyl]-3-yl)oxy)azetidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-boc-3-iodoazetidine (0.076 ml, 0.268 mmol) was added 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 (0.085 g, 0.134 mmol) and cesium carbonate (0.087 g, 0.268 mmol) in acetonitrile (0.335 ml) and stirred over night. LCMS indicated that the reaction was complete (mass—Boc group). 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 yield was assumed to be quantitative and taken directly on to the next step. m/z (ESI) 691.0 (M+1-Boc)+.

Workup

  1. washthe aqueous layer was washed 3× with DCM
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-fa1cdf3eeb7743c0bd29b37a191c35da
Source dataset
uspto-grants-2015_12
Patent number
US09212182B2

Reaction notes

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