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

HRID 1272986Notes

Reaction equation

HRID 1272986 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:28])[CH2:24][CH:25]([CH3:27])[CH3:26])[CH:19]=[CH:20][CH:21]=1)C.[NH2:29][NH:30][C:31](=O)[CH2:32][N:33]([CH3:35])[CH3:34].C[O-].[Na+]>CO>[CH3:34][N:33]([CH2:32][C:31]1[NH:30][N:29]=[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:28])[CH2:24][CH:25]([CH3:26])[CH3:27])[CH:19]=[CH:20][CH:21]=2)[N:5]=1)[CH3:35]

Participants

5

Reactant 3

HCID 683192-(Dimethylamino)acetohydrazideHCID 10942334Sodium MethoxideHCID 86585605N-{3-[5-(ethoxyiminomethyl)(1H-indazol-3-yl)]phenyl}-3-methylbutanamide hydrochloride

Product 1

HCID 22480072N-[3-(5-{5-[(Dimethylamino)Methyl](1H-1,2,4-Triazol-3-Yl)}(1H-Indazol-3-Yl))Phenyl]-3-Methylbutanamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was prepared according to example Example 329 C using N-{3-[5-(ethoxyiminomethyl)(1H-indazol-3-yl)]phenyl}-3-methylbutanamide hydrochloride (0.400 g, 0.997 mmol), N-amino-2-(dimethylamino)acetamide (0.350 g, 2.99 mmol) and sodium methoxide in methanol (0.348 mL, 4.37 M). The title compound was isolated after purification by preparative HPLC (0.074 g, 18% yield): 1H NMR (CD3OD) δ 8.73 (s, 1H), 8.19 (s, 1H), 8.08 (d, 1H), 7.75 (t, 2H), 7.69 (d, 1H), 7.51 (t, 1H), 3.81 (s, 2H), 2.45 (s, 6H), 2.3 (d, 2H), 2.21 (m, 1H), 1.04 (d, 6H); ES-MS (m/z) 418 [M+H]+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-2a8d8fa776684dacaf003e0a6c7618f7
Source dataset
uspto-grants-2007_04
Patent number
US07208513B2

Reaction notes

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