2-(Dimethylamino)acetohydrazide → HCID 178483336, compound

HRID 1349879Notes

Reaction equation

HRID 1349879 reaction equation
[CH:1]1([NH:5][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([CH:23]=[N:24]OCC)[CH:21]=4)[NH:16][N:15]=3)[CH:9]=2)=[O:7])[CH2:4][CH2:3][CH2:2]1.[NH2:28][NH:29][C:30](=O)[CH2:31][N:32]([CH3:34])[CH3:33].C[O-].[Na+]>CO>[CH3:33][N:32]([CH2:31][C:30]1[N:24]=[C:23]([C:20]2[CH:21]=[C:22]3[C:17](=[CH:18][CH:19]=2)[NH:16][N:15]=[C:14]3[C:10]2[CH:9]=[C:8]([C:6]([NH:5][CH:1]3[CH2:4][CH2:3][CH2:2]3)=[O:7])[CH:13]=[CH:12][CH:11]=2)[NH:28][N:29]=1)[CH3:34]

Participants

5

Reactant 3

HCID 683192-(Dimethylamino)acetohydrazideHCID 10942334Sodium MethoxideHCID 87827764HCID 87827764, compound

Product 1

HCID 178483336HCID 178483336, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The title compound was prepared according to the procedure of Example 367 C using N-cyclobutyl(3-[5-(ethoxyiminomethyl)(1H-indazol-3-yl)]phenyl)carboxamide.2HCl (460 mg, 1.06 mmol), N-amino-2-(dimethylamino) acetamide (372 mg, 3.17 mmol) and sodium methoxide (608 μL of a 25% w/w in methanol) in anhydrous methanol (7.0 mL) with a reaction time of 44 h. Purification of the residue by flash chromatography on silica gel with 50% methanol in ethyl acetate gave the desired product as a pale yellow solid. The residue was dissolved in a minimum amount of anhydrous methanol and excess 1.0 N HCl in anhydrous ethyl ether was added dropwise to precipitate the desired product as the bis-hydrochloride salt. The product was collected and dried under vacuum to afford the title compound (27 mg, 5% yield) as a light yellow powder. 1H NMR (DMSO-d6) δ 10.6 (br s, 1H), 8.89 (d, 1H), 8.84 (s, 1H), 8.4 (s, 1H), 8.17 (d, 1H), 8.12 (d, 1H), 7.91 (d, 1H), 7.76 (d, 1H), 7.63 (t, 1H), 4.5–4.4 (m, 1H), 4.44 (s, 2H), 2.83 (s, 6H), 2.23–2.0 (m, 4H), 1.72–1.62 (m, 2H); ES-MS (m/z) 416 [M+H]+ (HCl salt not detected).

Workup

  1. customThe title compound was prepared
  2. customwith a reaction time of 44 h
  3. customPurification of the residue by flash chromatography on silica gel with 50% methanol in ethyl acetate

Sources & evidence

ORD record
ord-2f46960b780b43b3afecbba2e62e04dc
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

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