Hydrochloric Acid → (E)-4-{3-amino-4-[2-(1H-indazol-3-yl)vinyl]-2-methoxyphenoxyacetyl}morpholine

HRID 1821435Notes

Reaction equation

HRID 1821435 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:27]=[CH:26][C:15]([O:16][CH2:17][C:18]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[O:19])=[C:14]([O:28][CH3:29])[C:13]=2[N+:30]([O-])=O)=[N:2]1.[Sn].Cl.[OH-].[Na+]>C(O)C>[NH2:30][C:13]1[C:14]([O:28][CH3:29])=[C:15]([CH:26]=[CH:27][C:12]=1/[CH:11]=[CH:10]/[C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][N:2]=1)[O:16][CH2:17][C:18]([N:20]1[CH2:21][CH2:22][O:23][CH2:24][CH2:25]1)=[O:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5352426Tin atomHCID 68999721HCID 68999721, compound

Product 1

HCID 69002052(E)-4-{3-amino-4-[2-(1H-indazol-3-yl)vinyl]-2-methoxyphenoxyacetyl}morpholineYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (E)-4-{4-[2-(1H-indazol-3-yl)vinyl]-2-methoxy-3-nitrophenoxyacetyl}morpholine (0.2 g, 0.46 mmol) obtained in Step 4 in ethanol (4.0 mL) was ice-cooled and the solution was added with tin (0.16 g, 1.4 mmol) and concentrated hydrochloric acid (2.0 mL), followed by stirring at room temperature for 3 hours. To the reaction mixture under ice-cooling, 6 mol/L sodium hydroxide was added to neutralize the mixture. Then, the obtained solid was filtered. The filtrate was added with saturated aqueous sodium hydrogencarbonate solution and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure to obtain (E)-4-{3-amino-4-[2-(1H-indazol-3-yl)vinyl]-2-methoxyphenoxyacetyl}morpholine (0.17 g, 93%).

Workup

  1. temperaturecooled
  2. temperatureTo the reaction mixture under ice-cooling
  3. filtrationThen, the obtained solid was filtered
  4. additionThe filtrate was added with saturated aqueous sodium hydrogencarbonate solution
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ee3d0292d6e94b2bb26e1423158b419d
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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