(4s)-2'-(3,6-Dihydro-2h-Pyran-4-Yl)-4'-Fluoro-7'-(2-Fluoropyridin-3-Yl)spiro[1,3-Oxazole-4,9'-Xanthen]-2-Amine → (S)-4'-fluoro-7'-(2-fluoropyridin-3-yl)-2'-(tetrahydro-2H-pyran-4-yl)-5H-spiro[oxazole-4,9'-xanthen]-2-amine

HRID 1970327Notes

Reaction equation

HRID 1970327 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]([C:22]5[C:23]([F:28])=[N:24][CH:25]=[CH:26][CH:27]=5)=[CH:14][CH:15]=4)[C@@:10]4([CH2:32][O:31][C:30]([NH2:33])=[N:29]4)[C:9]=3[CH:8]=2)[CH2:3][CH2:2]1>[Pd].CO>[F:21][C:19]1[C:18]2[O:17][C:16]3[C:11](=[CH:12][C:13]([C:22]4[C:23]([F:28])=[N:24][CH:25]=[CH:26][CH:27]=4)=[CH:14][CH:15]=3)[C@@:10]3([CH2:32][O:31][C:30]([NH2:33])=[N:29]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

4

Reactant 1

HCID 45254900(4s)-2'-(3,6-Dihydro-2h-Pyran-4-Yl)-4'-Fluoro-7'-(2-Fluoropyridin-3-Yl)spiro[1,3-Oxazole-4,9'-Xanthen]-2-Amine

Product 1

HCID 45255105(S)-4'-fluoro-7'-(2-fluoropyridin-3-yl)-2'-(tetrahydro-2H-pyran-4-yl)-5H-spiro[oxazole-4,9'-xanthen]-2-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(S)-2′-(3,6-dihydro-2H-pyran-4-yl)-4′-fluoro-7′-(2-fluoropyridin-3-yl)-5H-spiro[oxazole-4,9′-xanthen]-2-amine (30 mg, 0.067 mmol) and palladium on carbon (7.14 mg, 0.067 mmol) were combined in 10 ml of MeOH and stirred under an atmosphere of hydrogen overnight. The solution was filtered and concentrated to afford (S)-4′-fluoro-7′-(2-fluoropyridin-3-yl)-2′-(tetrahydro-2H-pyran-4-yl)-5H-spiro[oxazole-4,9′-xanthen]-2-amine as a white solid.

Workup

  1. filtrationThe solution was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-766a24c62b29460289cc1e2b9ff7663e
Source dataset
uspto-grants-2013_04
Patent number
US08426447B2

Reaction notes

Loading…