14352-51-3 → HCID 11950899, compound

HRID 734270Notes

Reaction equation

HRID 734270 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]=1.[CH:12]1([CH2:15][CH2:16][NH:17][C:18]([C:20]2[N:21]=[N:22][C:23]([N:26]3[CH2:31][CH2:30]N[CH2:28][CH2:27]3)=[CH:24][CH:25]=2)=[O:19])[CH2:14][CH2:13]1>C(O)C>[CH:12]1([CH2:15][CH2:16][NH:17][C:18]([C:20]2[N:21]=[N:22][C:23]([N:26]3[CH2:27][CH2:28][N:1]([C:2]4[C:10]5[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=5)[C:4](=[O:11])[N:3]=4)[CH2:30][CH2:31]3)=[CH:24][CH:25]=2)=[O:19])[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 8438114352-51-3HCID 66849327N-(2-cyclopropylethyl)-6-(1-piperazinyl)-3-pyridazinecarboxamide

Product 1

HCID 11950899HCID 11950899, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Aminoisoindol-1-one (0.292 g, 2.00 mmol) and 6-piperazin-1-ylpyridazine-3-carboxylic acid (2-cyclopropylethyl)amide (0.825 g, 3.00 mmol) were boiled together in ethanol (20 mL) for 48 hours. The solution was concentrated in vacuo. This residue was purified by column chromatography. The title compound was obtained as a white solid in 40% yield (0.328 g). 1H NMR (300 MHz, CDCl3) δ 8.07 (d, J=9.5 Hz, 1H), 7.97 (t, J=5.8 Hz, 1H), 7.76 (d, J=7.0 Hz, 1H), 7.64 (d, J=7.3 Hz, 1H), 7.52 (m, 1H), 7.01 (d, J=9.5 Hz, 1H), 4.42-4.35 (m, 4H), 4.23-4.20 (m, 2H), 3.93-3.89 (m, 2H), 3.54 (dd, J=6.7 and 13.2 Hz, 1H), 1.49 (m, 1H), 0.79-0.66 (m, 1H), 0.47-0.41 (m, 2H), 0.10-0.05 (m, 2H). 13C NMR (75 MHz, CDCl3) δ 181.5, 174.6, 162.9, 159.6, 145.6, 138.1, 134.9, 132.5, 131.7, 127.3, 124.0 123.3, 112.2, 47.2, 46.4 44.5, 43.2, 39.7, 34.5, 8.7, 4.2. MS (ES+) m/z 405.1 (M+1).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customThis residue was purified by column chromatography

Sources & evidence

ORD record
ord-623bd2a99f904bb98aa3e5bbe7de00b6
Source dataset
uspto-grants-2009_09
Patent number
US07592343B2

Reaction notes

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