Sodium Methoxide → HCID 178505579, compound

HRID 2183366Notes

Reaction equation

HRID 2183366 reaction equation
C(O[C:4]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[C:9]2[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)=[NH:5])C.[NH2:22][NH:23][C:24](=O)[CH2:25][O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C[O-].[Na+]>CO>[F:21][C:18]1[CH:17]=[CH:16][C:15]([C:9]2[C:8]3[C:12](=[CH:13][CH:14]=[C:6]([C:4]4[NH:22][N:23]=[C:24]([CH2:25][O:26][CH2:27][C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)[N:5]=4)[CH:7]=3)[NH:11][N:10]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 22479740ethoxy[3-(4-fluorophenyl)(1H-indazol-5-yl)]methanimineHCID 224803422-(Benzyloxy)acetohydrazide

Product 1

HCID 178505579HCID 178505579, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
90 °C

Procedure

To a suspension of ethoxy[3-(4-fluorophenyl)(1H-indazol-5-yl)]methanimine.2HCl (307 mg, 0.96 mmol) and N-amino-2-(phenylmethoxy)acetamide (259 mg, 1.44 mmol) in anhydrous methanol (3.0 mL) in a screw-top pressure tube was added freshly prepared sodium methoxide (615 μL of a 3.12 M solution in methanol). The tube was sealed and heated in a 90° C. oil bath for 17 h. The reaction was cooled, evaporated to dryness and partitioned between ethyl acetate and satd. NH4Cl. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated in vacuo to give an oily brown residue. Purification by flash chromatography on silica gel eluting with 5% methanol in dichloromethane (Rf=0.43) gave a pale solid (155 mg) which was re-chromatographed using 30% hexanes in ethyl acetate to remove traces of color.

Workup

  1. customThe tube was sealed
  2. temperatureThe reaction was cooled
  3. customevaporated to dryness
  4. custompartitioned between ethyl acetate and satd
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customto give an oily brown residue
  10. customPurification by flash chromatography on silica gel eluting with 5% methanol in dichloromethane (Rf=0.43)

Sources & evidence

ORD record
ord-0e3dd29f616f46008db11bc102cd43a8
Source dataset
uspto-grants-2005_05
Patent number
US06897231B2

Reaction notes

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