HCID 53464944, compound → HCID 53464882, compound

HRID 335923Notes

Reaction equation

HRID 335923 reaction equation
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[N:12]=[C:11]([F:13])[C:10]3[O:14][C:15]4[C:20]([C@@:21]5([CH2:25][O:24][C:23]([NH2:26])=[N:22]5)[C:9]=3[CH:8]=2)=[CH:19][C:18]([C:27]2[C:28]([F:33])=[N:29][CH:30]=[CH:31][CH:32]=2)=[CH:17][CH:16]=4)[CH2:3][CH2:2]1>[Pd]>[F:13][C:11]1[C:10]2[O:14][C:15]3[C:20]([C@@:21]4([CH2:25][O:24][C:23]([NH2:26])=[N:22]4)[C:9]=2[CH:8]=[C:7]([CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)[N:12]=1)=[CH:19][C:18]([C:27]1[C:28]([F:33])=[N:29][CH:30]=[CH:31][CH:32]=1)=[CH:17][CH:16]=3

Participants

3

Reactant 1

HCID 53464944HCID 53464944, compound

Product 1

HCID 53464882HCID 53464882, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A suspension of (S)-3-(3,6-dihydro-2H-pyran-4-yl)-1-fluoro-7-(2-fluoropyridin-3-yl)-5′H-spiro[chromeno[2,3-c]pyridine-5,4′-oxazol]-2′-amine (60 mg, 0.134 mmol; prepared as described in Method BB33) and 10% Pd/C (60 mg) was stirred at rt under 1 atm of H2 gas for 12 hours. The suspension was filtered through a pad of silica gel washing with a 1:1 mixture of CH2Cl2/MeOH. The filtrate was evaporated to dryness and purified by silica gel chromatography (EtOAc to EtOAc/MeOH=100:5 to 100:7) to provide (S)-1-fluoro-7-(2-fluoropyridin-3-yl)-3-(tetrahydro-2H-pyran-4-yl)-5′H-spiro[chromeno[2,3-c]pyridine-5,4′-oxazol]-2′-amine as an off-white solid.

Workup

  1. filtrationThe suspension was filtered through a pad of silica gel washing with a 1:1 mixture of CH2Cl2/MeOH
  2. customThe filtrate was evaporated to dryness
  3. custompurified by silica gel chromatography (EtOAc to EtOAc/MeOH=100:5 to 100:7)

Sources & evidence

ORD record
ord-1cfeaa9f34b44fecb19693ca5778d8f5
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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