HCID 117600815, compound → HCID 117600782, compound

HRID 931662Notes

Reaction equation

HRID 931662 reaction equation
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:20]=[C:19]([F:21])[C:18]3[O:17][C:16]4[C:11](=[CH:12][C:13]([NH2:22])=[CH:14][CH:15]=4)[C@@:10]4([CH2:27][CH2:26][O:25][C:24]([NH2:28])=[N:23]4)[C:9]=3[CH:8]=2)[CH2:3][CH2:2]1.[H][H]>CCO.[Pd]>[F:21][C:19]1[C:18]2[O:17][C:16]3[C:11](=[CH:12][C:13]([NH2:22])=[CH:14][CH:15]=3)[C@@:10]3([CH2:27][CH2:26][O:25][C:24]([NH2:28])=[N:23]3)[C:9]=2[CH:8]=[C:7]([CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)[CH:20]=1

Participants

5

Reactant 2

HCID 117600815HCID 117600815, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 117600782HCID 117600782, compoundYield 20.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The (S)-2′-(3,6-dihydro-2H-pyran-4-yl)-4′-fluoro-5,6-dihydrospiro[[1,3]oxazine-4,9′-xanthene]-2,7′-diamine (0.231 g, 0.606 mmol) was taken up in EtOH (2 mL). Palladium (10%) on carbon (0.090 g, 0.084 mmol) was added. A 1-L balloon filled with hydrogen was emptied into the flask, venting through a needle. The vent was removed, and another 1-L balloon was attached. The reaction was stirred at RT overnight. The reaction was filtered through Celite, rinsing with 10% MeOH-DCM (60 mL). The filtrate was concentrated. The residue was purified through silica gel (35 mL) which had been deactivated with Et3N (3.5 mL), eluting with 4% to 8% MeOH-DCM containing 1% v/v Et3N, affording (S)-4′-fluoro-2′-(tetrahydro-2H-pyran-4-yl)-5,6-dihydrospiro[[1,3]oxazine-4,9′-xanthene]-2,7′-diamine (48 mg, 0.123 mmol). MS m/z=384 [M+H]+.

Workup

  1. customThe vent was removed
  2. filtrationThe reaction was filtered through Celite
  3. washrinsing with 10% MeOH-DCM (60 mL)
  4. concentrationThe filtrate was concentrated
  5. customThe residue was purified through silica gel (35 mL) which
  6. washeluting with 4% to 8% MeOH-DCM containing 1% v/v Et3N

Sources & evidence

ORD record
ord-f48e87186f924bca8191ab1ca502d04e
Source dataset
uspto-grants-2016_03
Patent number
US09296759B2

Reaction notes

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