(S)-3-chloro-7-(pyridin-3-yl)-5'H-spiro[chromeno[2,3-c]pyridine-5,4'-oxazol]-2'-amine → (S)-7-(pyridin-3-yl)-5'H-spiro[chromeno[2,3-c]pyridine-5,4'-oxazol]-2'-amine

HRID 335756Notes

Reaction equation

HRID 335756 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]2[O:8][C:9]3[C:14]([C@@:15]4([CH2:19][O:18][C:17]([NH2:20])=[N:16]4)[C:4]=2[CH:3]=1)=[CH:13][C:12]([C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)=[CH:11][CH:10]=3>CO.[Pd]>[N:23]1[CH:24]=[CH:25][CH:26]=[C:21]([C:12]2[CH:13]=[C:14]3[C@@:15]4([CH2:19][O:18][C:17]([NH2:20])=[N:16]4)[C:4]4[CH:3]=[CH:2][N:7]=[CH:6][C:5]=4[O:8][C:9]3=[CH:10][CH:11]=2)[CH:22]=1

Participants

4

Reactant 1

HCID 58466185(S)-3-chloro-7-(pyridin-3-yl)-5'H-spiro[chromeno[2,3-c]pyridine-5,4'-oxazol]-2'-amine

Product 1

HCID 58466160(S)-7-(pyridin-3-yl)-5'H-spiro[chromeno[2,3-c]pyridine-5,4'-oxazol]-2'-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To the solution of (S)-3-chloro-7-(pyridin-3-yl)-5′H-spiro[chromeno[2,3-c]pyridine-5,4′-oxazol]-2′-amine (23 mg, 0.063 mmol) in MeOH (2 mL) was added 10% Pd on Carbon (10 mg, 0.073 mmol). The mixture was hydrogenated under 1 atm of H2 for 24 h. After filtration and concentration, the crude material was absorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (12 g), eluting with isocratic % to 20% MeOH in CH2CL2, to provide (S)-7-(pyridin-3-yl)-5′H-spiro[chromeno[2,3-c]pyridine-5,4′-oxazol]-2′-amine as white solid.

Workup

  1. filtrationAfter filtration and concentration
  2. customthe crude material was absorbed onto a plug of silica gel
  3. custompurified by chromatography through a Redi-Sep pre-packed silica gel column (12 g)
  4. washeluting with isocratic % to 20% MeOH in CH2CL2

Sources & evidence

ORD record
ord-637761189dba404da48cfbb39f2b970c
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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