2-(Dimethylamino)acetohydrazide → HCID 178483334, compound

HRID 1349877Notes

Reaction equation

HRID 1349877 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([CH:22]=[N:23]OCC)[CH:20]=4)[NH:15][N:14]=3)[CH:8]=2)=[O:6])[CH2:3][CH2:2]1.[NH2:27][NH:28][C:29](=O)[CH2:30][N:31]([CH3:33])[CH3:32].C[O-].[Na+]>CO>[CH3:32][N:31]([CH2:30][C:29]1[N:23]=[C:22]([C:19]2[CH:20]=[C:21]3[C:16](=[CH:17][CH:18]=2)[NH:15][N:14]=[C:13]3[C:9]2[CH:8]=[C:7]([C:5]([NH:4][CH:1]3[CH2:2][CH2:3]3)=[O:6])[CH:12]=[CH:11][CH:10]=2)[NH:27][N:28]=1)[CH3:33]

Participants

5

Reactant 3

HCID 683192-(Dimethylamino)acetohydrazideHCID 10942334Sodium MethoxideHCID 87828915HCID 87828915, compound

Product 1

HCID 178483334HCID 178483334, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The title compound was prepared according to the procedure of Example 367 C using N-cyclopropyl(3-[5-(ethoxyiminomethyl)(1H-indazol-3-yl)]phenyl)carboxamide.2HCl (377 mg, 0.89 mmol), N-amino-2-(dimethylamino) acetamide (315 mg, 2.69 mmol) and sodium methoxide (515 μL of a 25% w/w in methanol) in anhydrous methanol (5.0 mL) with a reaction time of 24 h. Purification of the residue by flash chromatography on silica gel with 50% methanol in ethyl acetate gave the desired product as a light orange solid. Further purification by preparatory TLC using 50% methanol in ethyl acetate afforded the title compound (145 mg, 40% yield) as an off-white powder. 1H NMR (DMSO-d6) δ 8.8 (br d, 1H), 8.7 (s, 1H), 8.4 (s, 1H), 8.14–8.05 (m, 2H), 7.84 (d, 1H), 7.7–7.6 (m, 2H), 3.55 (s, 2H), 2.92–2.85 (m, 1H), 2.2 (s, 6H); ES-MS (m/z) 402 [M+H]+.

Workup

  1. customThe title compound was prepared
  2. customwith a reaction time of 24 h
  3. customPurification of the residue by flash chromatography on silica gel with 50% methanol in ethyl acetate

Sources & evidence

ORD record
ord-f839f51d5ae94bd89028a60519c5fdf0
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

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