2-(Dimethylamino)acetohydrazide → HCID 11711025, compound

HRID 1349917Notes

Reaction equation

HRID 1349917 reaction equation
C(O[C:4]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[C:9]2[C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[C:20]([O:25][CH3:26])[CH:21]=2)[CH:16]=1)=[NH:5])C.[NH2:27][NH:28][C:29](=O)[CH2:30][N:31]([CH3:33])[CH3:32].C[O-].[Na+]>CO>[CH3:26][O:25][C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15]([C:9]1[C:8]3[C:12](=[CH:13][CH:14]=[C:6]([C:4]4[N:5]=[C:29]([CH2:30][N:31]([CH3:33])[CH3:32])[NH:28][N:27]=4)[CH:7]=3)[NH:11][N:10]=1)[CH:24]=[CH:23]2

Participants

5

Reactant 3

HCID 683192-(Dimethylamino)acetohydrazideHCID 10942334Sodium MethoxideHCID 21101190HCID 21101190, compound

Product 1

HCID 11711025HCID 11711025, compoundYield 5.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
95 °C

Procedure

To a suspension of ethoxy[3-(6-methoxy(2-naphthyl))(1H-indazol-5-yl)]methanimine (0.430 g, 1.13 mmol) in methanol (5 mL) was added N-amino-2-(dimethylamino)acetamide (0.396 g, 3.38 mmol) and 4.3 M sodium methoxide (0.578 mL, 2.49 mmol). The mixture was heated in a sealed tube at 95° C. for 16 h. The solvent was removed using a rotary evaporator and gave a solid residue. Purification of the residue by preparative HPLC (10–80%, acetonitrile/water) gave the title compound (0.025 g, 5% yield): 1H NMR (DMSO-d6) δ 13.95 (br s, 1H), 13.40 (br s, 1H), 8.73 (s, 1H), 8.44 (s, 1H), 8.09 (t, 2H), 8.00 (t, 2H), 7.68 (d, 1H), 7.39 (d, 1H), 7.21 (dd, 1H), 3.90 (s, 3H), 3.60 (s, 2H), 2.22 (s, 6H); ES-MS (m/z) 399 [M+1]+.

Workup

  1. customThe solvent was removed
  2. customa rotary evaporator
  3. customgave a solid residue
  4. customPurification of the residue by preparative HPLC (10–80%, acetonitrile/water)

Sources & evidence

ORD record
ord-b56bac05bc344db7bbb322a19fd694db
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

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