Tetrahydrofuran → HCID 89963035, compound

HRID 337873Notes

Reaction equation

HRID 337873 reaction equation
[CH3:1][O:2][C:3]1[CH:48]=[C:47]([O:49][CH3:50])[CH:46]=[CH:45][C:4]=1[CH2:5][N:6]([C:39]1[CH:44]=[CH:43][N:42]=[CH:41][N:40]=1)[S:7]([C:10]1[CH:15]=[C:14]([CH3:16])[C:13]([O:17][C@H:18]2[CH2:23][CH2:22][CH2:21][CH2:20][C@@H:19]2[C:24]2[C:25]([N+:35]([O-])=O)=[N:26][N:27]([CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][O:30]3)[CH:28]=2)=[CH:12][C:11]=1[F:38])(=[O:9])=[O:8].C1COCC1.[BH4-].[Na+].C(=O)([O-])O.[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(OCC)(=O)C.C(O)C>[NH2:35][C:25]1[C:24]([C@H:19]2[CH2:20][CH2:21][CH2:22][CH2:23][C@@H:18]2[O:17][C:13]2[C:14]([CH3:16])=[CH:15][C:10]([S:7]([N:6]([CH2:5][C:4]3[CH:45]=[CH:46][C:47]([O:49][CH3:50])=[CH:48][C:3]=3[O:2][CH3:1])[C:39]3[CH:44]=[CH:43][N:42]=[CH:41][N:40]=3)(=[O:9])=[O:8])=[C:11]([F:38])[CH:12]=2)=[CH:28][N:27]([CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][O:30]2)[N:26]=1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 89963357HCID 89963357, compound

Product 1

HCID 89963035HCID 89963035, compoundYield 42.1%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the N-(2,4-dimethoxybenzyl)-2-fluoro-5-methyl-4-({(1S*,2R*)-2-[3-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl]cyclohexyl}oxy)-N-(pyrimidin-4-yl)benzenesulfonamide (193 mg, 0.272 mmol) prepared in Example 68a and bis(acetylacetonato)copper (II) (21.3 mg, 0.0815 mmol) in a mixed solvent of THF (4.0 mL) and ethanol (4.0 mL), sodium borohydride (101 mg, 2.66 mmol) was added, and the reaction solution was stirred at room temperature for 20 minutes. To the reaction solution, a saturated aqueous solution of sodium hydrogencarbonate (10 mL) and ethyl acetate (10 mL) were added, the mixture was filtered through celite, and the filtrate was subjected to extraction. The thus obtained organic layer was dried over anhydrous sodium sulfate. After vacuum concentration, the residue was purified with silica gel chromatography to yield the title compound (78 mg, 42%) as a light brown amorphous solid.

Workup

  1. filtrationthe mixture was filtered through celite
  2. extractionthe filtrate was subjected to extraction
  3. dry with materialThe thus obtained organic layer was dried over anhydrous sodium sulfate
  4. concentrationAfter vacuum concentration
  5. customthe residue was purified with silica gel chromatography

Sources & evidence

ORD record
ord-03a92a629de44b8bba03594c9a24d2c7
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

Loading…