3-Chloro-6-(pyridin-3-yl)pyridazine → HCID 57654477, compound

HRID 1921641Notes

Reaction equation

HRID 1921641 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:12][C:13]([NH:15][NH2:16])=O)[CH:8]=2)[N:3]=1.Cl[C:18]1[N:19]=[N:20][C:21]([C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)=[CH:22][CH:23]=1>C(O)CCC>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:12][C:13]3[N:19]4[N:20]=[C:21]([C:24]5[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=5)[CH:22]=[CH:23][C:18]4=[N:16][N:15]=3)[CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 167324353-Chloro-6-(pyridin-3-yl)pyridazineHCID 57654536HCID 57654536, compound

Product 1

HCID 57654477HCID 57654477, compoundYield 35.9%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

(2-Chloro-quinolin-6-yl)-acetic acid hydrazide (0.030 g, 0.127 mmol) and 3-chloro-6-pyridin-3-yl-pyridazine (0.024 g, 0.127 mmol) were heated to reflux in butanol (0.5 mL) for several hours. The reaction was cooled to room temperature and filtered. The filtrate was purified via reverse phase HPLC on a C18 column eluting with acetonitrile in water (0.1% TFA) to give 0.017 g (35%) of 2-chloro-6-(6-pyridin-3-yl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl)-quinoline. 1H NMR (400 MHz, CD3OD) δ 9.38 (m, 1H), 8.88 (d, 1H, J=5.2 Hz), 8.85 (m, 1H), 8.42 (d, 1H, J=9.6 Hz), 8.31 (d, 1H, J=8.8 Hz), 8.06 (s, 1H), 8.03 (m, 1H), 7.92 (m, 3H), 7.50 (d, 1H, J=8.8 Hz), 4.93 (s, 2H). Mass spectrum (LCMS, ESI pos.): Calcd for C20H13ClN6; found: 373.3, 375.3 (M+H).

Workup

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

Sources & evidence

ORD record
ord-72ca8fde506442c1afd17891aca7ab01
Source dataset
uspto-grants-2012_05
Patent number
US08173654B2

Reaction notes

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