2-(Dimethylamino)acetohydrazide → (2R)-N-[3-(5-{5-[(Dimethylamino)Methyl](1H-1,2,4-Triazol-3-Yl)}(1H-Indazol-3-Yl))Phenyl]-2-Hydroxy-2-Phenylacetamide

HRID 1353890Notes

Reaction equation

HRID 1353890 reaction equation
Cl.C(O[N:5]=[CH:6][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:17]=[C:18]([NH:22][C:23](=[O:32])[C@H:24]([OH:31])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:19]=[CH:20][CH:21]=1)C.[NH2:33][NH:34][C:35](=O)[CH2:36][N:37]([CH3:39])[CH3:38].C[O-].[Na+]>CO>[CH3:38][N:37]([CH2:36][C:35]1[NH:34][N:33]=[C:6]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[NH:12][N:11]=[C:10]3[C:16]2[CH:17]=[C:18]([NH:22][C:23](=[O:32])[C@H:24]([OH:31])[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:19]=[CH:20][CH:21]=2)[N:5]=1)[CH3:39]

Participants

5

Reactant 3

HCID 683192-(Dimethylamino)acetohydrazideHCID 10942334Sodium MethoxideHCID 86585601(2R)-N-{3-[5-(ethoxyiminomethyl)(1H-indazol-3-yl)]phenyl}-2-hydroxy-2-phenylacetamide hydrochloride

Product 1

HCID 20788990(2R)-N-[3-(5-{5-[(Dimethylamino)Methyl](1H-1,2,4-Triazol-3-Yl)}(1H-Indazol-3-Yl))Phenyl]-2-Hydroxy-2-PhenylacetamideYield 9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a suspension of (2R)-N-{3-[5-(ethoxyiminomethyl)(1H-indazol-3-yl)]phenyl}-2-hydroxy-2-phenylacetamide hydrochloride (0.500 g, 1.11 mmol) in methanol (10 mL) were added 3 equivalents of N-amino-2-(dimethylamino)acetamide (0.390 g, 3.33 mmol) and 2.5 equivalents of sodium methoxide in methanol (0.635 mL, 4.3 M). After stirring at room temperature for 1 h, the reaction mixture was heated to 95° C. for 48 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 (0.050 g, 9% yield): 1H NMR (CD3OD) δ 8.72 (s, 1H), 8.23 (s, 1H), 8.08 (d, 1H), 7.89 (d, 2H), 7.68 (d, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.40–7.32 (m, 3H), 5.21 (s, 1H), 3.71 (s, 2H), 2.37 (s, 6H); ES-MS (m/z) 468 [M+H]+.

Workup

  1. temperaturethe reaction mixture was heated to 95° C. for 48 hours
  2. customThe reaction was then quenched with water
  3. extractionextracted with ethyl acetate
  4. customThe title compound was purified by preparative HPLC (0.050 g, 9% yield)

Sources & evidence

ORD record
ord-1278d466a66241ec8a03ce37df161845
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

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