Sodium Methoxide → HCID 67383505, compound

HRID 335869Notes

Reaction equation

HRID 335869 reaction equation
F[C:2]1[C:7]2[O:8][C:9]3[C:14]([C@@:15]4([CH2:19][O:18][C:17]([NH2:20])=[N:16]4)[C:6]=2[CH:5]=[C:4]([C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)[N: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.[CH3:33][O-:34].[Na+]>CO>[CH3:33][O:34][C:2]1[C:7]2[O:8][C:9]3[C:14]([C@@:15]4([CH2:19][O:18][C:17]([NH2:20])=[N:16]4)[C:6]=2[CH:5]=[C:4]([C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)[N: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

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 58466157HCID 58466157, compound

Product 1

HCID 67383505HCID 67383505, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (S)-1-fluoro-3,7-di(pyridin-3-yl)-5′H-spiro[chromeno[2,3-c]pyridine-5,4′-oxazol]-2′-amine (40 mg, 0.094 mmol) and sodium methoxide (52.4 μL, 0.940 mmol) in 15 mL of MeOH was heated to 65° for 5 h. After cooling to rt, the reaction was evaporated to dryness and was partitioned between water (100 mL) and EtOAc (100 mL). The layers were separated and the organics were dried over sodium sulfate, filtered and evaporated to dryness. Flash column (CH2Cl2 to CH2Cl2/MeOH=100:5 to 100:10 to 100:20) gave (S)-1-methoxy-3,7-di(pyridin-3-yl)-5′H-spiro[chromeno[2,3-c]pyridine-5,4′-oxazol]-2′-amine as an off white solid.

Workup

  1. customthe reaction was evaporated to dryness
  2. customwas partitioned between water (100 mL) and EtOAc (100 mL)
  3. customThe layers were separated
  4. dry with materialthe organics were dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-ca3c27d7322744f6a8650cb9aa51edb1
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

Loading…