HCID 67383293, compound → HCID 58466204, compound

HRID 335840Notes

Reaction equation

HRID 335840 reaction equation
[NH2:1][C:2]1[O:3][CH2:4][C@:5]2([N:32]=1)[C:18]1[CH:17]=[C:16]([C:19]3[CH:20]=[N:21][CH:22]=[N:23][CH:24]=3)[C:15]([F:25])=[CH:14][C:13]=1[O:12][C:11]1[C:6]2=[CH:7][C:8]([C:26]#[C:27][C:28]([CH3:31])([OH:30])[CH3:29])=[CH:9][CH:10]=1>CO.[Pd]>[NH2:1][C:2]1[O:3][CH2:4][C@:5]2([N:32]=1)[C:18]1[CH:17]=[C:16]([C:19]3[CH:24]=[N:23][CH:22]=[N:21][CH:20]=3)[C:15]([F:25])=[CH:14][C:13]=1[O:12][C:11]1[C:6]2=[CH:7][C:8]([CH2:26][CH2:27][C:28]([CH3:29])([OH:30])[CH3:31])=[CH:9][CH:10]=1

Participants

4

Reactant 1

HCID 67383293HCID 67383293, compound

Product 1

HCID 58466204HCID 58466204, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A vial charged with (R)-4-(2-amino-3′-fluoro-2′-(pyrimidin-5-yl)-5H-spiro[oxazole-4,9′-xanthene]-7′-yl)-2-methylbut-3-yn-2-ol (0.050 g, 0.116 mmol) and 10% Pd/C (1.236 mg, 0.012 mmol) was taken up in 5 mL MeOH thoroughly degassed then placed under 50 psi H2 overnight. The reaction mixture was filtered through celite and concentrated in vacuo to provide an off white solid. Purification of the crude residue by column chromatography [0-80% (9:1:0.1—CH2Cl2:MeOH:NH4OH)/CH2Cl2] gave (R)-4-(2-amino-3′-fluoro-2′-(pyrimidin-5-yl)-5H-spiro[oxazole-4,9′-xanthene]-7′-yl)-2-methylbutan-2-ol. MS m/z=435.0 [M+H].

Workup

  1. customthoroughly degassed
  2. customthen placed under 50 psi H2 overnight
  3. filtrationThe reaction mixture was filtered through celite and
  4. concentrationconcentrated in vacuo
  5. customto provide an off white solid
  6. customPurification of the crude residue by column chromatography [0-80% (9:1:0.1—CH2Cl2:MeOH:NH4OH)/CH2Cl2]

Sources & evidence

ORD record
ord-b009648f76c3449596c46b20a33baad0
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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