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

HRID 2183334Notes

Reaction equation

HRID 2183334 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:29])[CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:19]=[CH:20][CH:21]=1)C.[NH2:30][NH:31][C:32](=O)[CH2:33][N:34]([CH3:36])[CH3:35].C[O-].[Na+]>CO>[CH3:35][N:34]([CH2:33][C:32]1[NH:31][N:30]=[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:29])[CH2:24][C:25]([CH3:26])([CH3:28])[CH3:27])[CH:19]=[CH:20][CH:21]=2)[N:5]=1)[CH3:36]

Participants

5

Reactant 3

HCID 683192-(Dimethylamino)acetohydrazideHCID 10942334Sodium MethoxideHCID 86585603N-{3-[5-(ethoxyiminomethyl)(1H-indazol-3-yl)]phenyl}-3,3-dimethylbutanamide hydrochloride

Product 1

HCID 22479849N-[3-(5-{5-[(Dimethylamino)Methyl](1H-1,2,4-Triazol-3-Yl)}(1H-Indazol-3-Yl))Phenyl]-3,3-Dimethylbutanamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was prepared according to the procedure described in Example 329 C using N-{3-[5-(ethoxyiminomethyl)(1H-indazol-3-yl)]phenyl}-3,3-dimethylbutanamide hydrochloride (0.360 g, 0.87 mmol), N-amino-2-(dimethylamino)acetamide (0.304 g, 2.60 mmol) and sodium methoxide in methanol (0.398 mL, 4.37 M). The title compound was isolated after purification by preparative HPLC (0.093 g, 25% yield): 1H NMR (CD3OD) δ 8.72 (s, 1H), 8.16 (t, 1H), 8.08 (dt, 1H), 7.75 (dt, 2H), 7.66 (d, 1H), 7.50 (t, 1H), 3.71 (s, 2H), 2.37 (s, 6H), 2.30 (s, 2H), 1.12 (s, 9H); ES-MS (m/z) 432 [M+H]+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-9e8c64d52e324c97b75193616f2671ff
Source dataset
uspto-grants-2005_05
Patent number
US06897231B2

Reaction notes

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