3-Chloro-6-(pyridin-3-yl)pyridazine → HCID 57654553, compound

HRID 1661823Notes

Reaction equation

HRID 1661823 reaction equation
[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:6]([CH2:7][N:8]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH2:19][C:20]([NH:22][NH2:23])=O)[CH:15]=3)[N:10]=[CH:9]2)=[CH:5][CH:4]=1.Cl[C:27]1[N:28]=[N:29][C:30]([C:33]2[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=2)=[CH:31][CH:32]=1>C(O)CCC>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH2:19][C:20]4[N:22]5[N:23]=[C:30]([C:33]6[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=6)[CH:31]=[CH:32][C:27]5=[N:28][N:29]=4)[CH:15]=3)[N:10]=[CH:9]2)=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 167324353-Chloro-6-(pyridin-3-yl)pyridazineHCID 57654578HCID 57654578, compound

Product 1

HCID 57654553HCID 57654553, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

[3-(4-Methoxy-benzyl)-4-oxo-3,4-dihydro-quinazolin-6-yl]-acetic acid hydrazide (0.024 g, 0.071 mmol) and 3-chloro-6-pyridin-3-yl-pyridazine (0.012 g, 0.063 mmol) were heated to 130° C. in butanol (0.5 mL) for several hours. The compound was purified via reverse phase HPLC on a C18 column eluting with acetonitrile in water (0.1% TFA) to give 0.016 g (53%) of 3-(4-methoxy-benzyl)-6-(6-pyridin-3-yl [1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl)-3H quinazolin-4-one. 1H NMR (400 MHz, CDCl3) δ 9.08 (m, 1H), 8.71 (dd, 1H, J=4.8, 1.6 Hz), 8.39 (m, 1H), 8.25 (m, 1H, 8.13 (d, 1H, J=9.6 Hz), 7.99 (s, 1H), 7.77 (dd, 1H, J=8.4, 2.0 Hz), 7.58 (d, 1H, J=8.4 Hz), 7.48 (d, 1H, J=9.6 Hz), 7.41 (m, 1H), 7.21 (d, 2H, J=8.4 Hz), 6.77 (d, 2H, J=8.8 Hz), 5.05 (s, 2H), 5.05 (s, 2H), 4.71 (s, 2H), 3.70 (s, 3H). Mass spectrum (LCMS, ESI pos.): Calcd for C27H21N7O2; found: 476.1, 477.2 (M+H).

Workup

  1. customThe compound was purified via reverse phase HPLC on a C18 column
  2. washeluting with acetonitrile in water (0.1% TFA)

Sources & evidence

ORD record
ord-8d5171b0685049899b153bdaeb4c02c4
Source dataset
uspto-grants-2011_10
Patent number
US08030305B2

Reaction notes

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