(S)-4-(2-amino-5'-fluoro-2'-(2-fluoropyridin-3-yl)-5H-spiro[oxazole-4,9'-xanthene]-7'-yl)-2-methylbut-3-yn-2-ol → (S)-4-(2-amino-5'-fluoro-2'-(2-fluoropyridin-3-yl)-5H-spiro[oxazole-4,9'-xanthene]-7'-yl)-2-methylbutan-2-ol

HRID 335832Notes

Reaction equation

HRID 335832 reaction equation
[NH2:1][C:2]1[O:3][CH2:4][C@:5]2([N:33]=1)[C:18]1[CH:17]=[C:16]([C:19]3[C:20]([F:25])=[N:21][CH:22]=[CH:23][CH:24]=3)[CH:15]=[CH:14][C:13]=1[O:12][C:11]1[C:6]2=[CH:7][C:8]([C:27]#[C:28][C:29]([CH3:32])([OH:31])[CH3:30])=[CH:9][C:10]=1[F:26].[H][H]>[Pd]>[NH2:1][C:2]1[O:3][CH2:4][C@:5]2([N:33]=1)[C:18]1[CH:17]=[C:16]([C:19]3[C:20]([F:25])=[N:21][CH:22]=[CH:23][CH:24]=3)[CH:15]=[CH:14][C:13]=1[O:12][C:11]1[C:6]2=[CH:7][C:8]([CH2:27][CH2:28][C:29]([CH3:30])([OH:31])[CH3:32])=[CH:9][C:10]=1[F:26]

Participants

4

Reactant 2

HCID 67383734(S)-4-(2-amino-5'-fluoro-2'-(2-fluoropyridin-3-yl)-5H-spiro[oxazole-4,9'-xanthene]-7'-yl)-2-methylbut-3-yn-2-olHCID 178418361HCID 178418361, compound

Product 1

HCID 53464879(S)-4-(2-amino-5'-fluoro-2'-(2-fluoropyridin-3-yl)-5H-spiro[oxazole-4,9'-xanthene]-7'-yl)-2-methylbutan-2-ol

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A 100 ml flask was charged with (S)-4-(2-amino-5′-fluoro-2′-(2-fluoropyridin-3-yl)-5H-spiro[oxazole-4,9′-xanthene]-7′-yl)-2-methylbut-3-yn-2-ol (120 mg, 0.268 mmol) ethanol (4 ml). Palladium on carbon (86 mg, 0.080 mmol) was added under argon and the resulting mixture was hydrogenated under 1 atm of hydrogen gas for 1 hr. The mixture was filtered through celite and concentrated in vacuo to provide (S)-4-(2-amino-5′-fluoro-2′-(2-fluoropyridin-3-yl)-5H-spiro[oxazole-4,9′-xanthene]-7′-yl)-2-methylbutan-2-ol. MS m/z=454.0 [M+H].

Workup

  1. filtrationThe mixture was filtered through celite and
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0b09f4ad8287481cb8124440e257a6dc
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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