Sodium Methoxide → HCID 20789019, compound

HRID 1349835Notes

Reaction equation

HRID 1349835 reaction equation
Cl.C(O[C:5]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][N:11]=[C:10]2[C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)=[NH:6])C.[NH2:23][NH:24][C:25](=O)[CH2:26][NH:27][CH3:28].C[O-].[Na+]>CO>[F:22][C:19]1[CH:20]=[CH:21][C:16]([C:10]2[C:9]3[C:13](=[CH:14][CH:15]=[C:7]([C:5]4[N:6]=[C:25]([CH2:26][NH:27][CH3:28])[NH:24][N:23]=4)[CH:8]=3)[NH:12][N:11]=2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 22479739ethoxy[3-(4fluorophenyl)(1H-indazol-5-yl)]methanimine hydrochlorideHCID 224799682-(Methylamino)acetohydrazide

Product 1

HCID 20789019HCID 20789019, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A suspension of ethoxy[3-(4-fluorophenyl)(1H-indazol-5-yl)]methanimine hydrochloride (0.300 g, 0.94 mmol) and N-amino-2-(methylamino)acetamide (0.290 g, 2.81 mmol) in 4 mL of anhydrous methanol was prepared. An excess of a commercial solution of sodium methoxide in methanol (0.643 mL, 4.37 M) was added. After an hour, the temperature was raised to reflux and was maintained for 48 hours although no further conversion was observed after 24 hours. The reaction was then quenched with water, the pH adjusted to neutral and the crude product extracted with ethyl acetate. The title compound was purified by preparative HPLC (0.034 g, 11% yield): 1H NMR (CD3OD) δ 8.71 (s, 1H), 8.11–8.03 (m, 3H), 7.69 (d, 1H), 7.3 (t, 2H), 3.95 (s, 2H), 2.49 (s, 3H); ES-MS (m/z) 323 [M+H]+.

Workup

  1. customwas prepared
  2. waitAfter an hour
  3. temperaturethe temperature was raised
  4. temperatureto reflux
  5. temperaturewas maintained for 48 hours although no further conversion
  6. customThe reaction was then quenched with water
  7. extractionextracted with ethyl acetate
  8. customThe title compound was purified by preparative HPLC (0.034 g, 11% yield)

Sources & evidence

ORD record
ord-07ea6ae4aa3b4a9ba24f7eb8596c2e75
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

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