2-(Dimethylamino)acetohydrazide → n-[3-(5-{5-[(Dimethylamino)methyl](1h-1,2,4-triazol-3-yl)}(1h-indazol-3-yl))phenyl]-3-pyridylcarboxamide

HRID 2183337Notes

Reaction equation

HRID 2183337 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]([C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)=[O:24])[CH:19]=[CH:20][CH:21]=1)C.[NH2:31][NH:32][C:33](=O)[CH2:34][N:35]([CH3:37])[CH3:36].C[O-].[Na+]>CO>[CH3:36][N:35]([CH2:34][C:33]1[NH:32][N:31]=[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]([C:25]3[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=3)=[O:24])[CH:19]=[CH:20][CH:21]=2)[N:5]=1)[CH3:37]

Participants

5

Reactant 3

HCID 683192-(Dimethylamino)acetohydrazideHCID 10942334Sodium MethoxideHCID 87828228n-{3-[5-(Ethoxyiminomethyl)(1h-indazol-3-yl)]phenyl}-3-pyridylcarboxamide hydrochloride

Product 1

HCID 22480091n-[3-(5-{5-[(Dimethylamino)methyl](1h-1,2,4-triazol-3-yl)}(1h-indazol-3-yl))phenyl]-3-pyridylcarboxamide

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-pyridylcarboxamide hydrochloride (0.400 g, 0.873 mmol), N-amino-2-(dimethylamino)acetamide (0.306 g, 2.62 mmol) and sodium methoxide in methanol (0.609 mL, 4.37 M). The title compound was isolated after purification by preparative HPLC (0.037 g, 10% yield): 1H NMR (CD3OD) δ 9.16 (dd, 1H), 8.79 (d, 1H), 8.75 (dd, 1H), 8.43 (dt, 1H), 8.39 (s, 1H), 8.09 (dd, 1H), 7.89-7.83 (m, 2H), 7.72 (d, 1H), 7.65-7.56 (m, 2H), 4.06 (br s, 2H), 2.61 (br s, 6H); ES-MS (m/z) 439 [M+H]+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-ca35f82da4c54501b0e0dc1b2fc93f20
Source dataset
uspto-grants-2005_05
Patent number
US06897231B2

Reaction notes

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