3-Chloro-6-(1-methyl-1H-pyrazol-4-yl)pyridazine → HCID 57654475, compound

HRID 1661828Notes

Reaction equation

HRID 1661828 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][C:12]([NH:14][NH2:15])=O)=[CH:8][CH:9]=2)[CH:4]=[N:3][CH:2]=1.Cl[C:17]1[N:18]=[N:19][C:20]([C:23]2[CH:24]=[N:25][N:26]([CH3:28])[CH:27]=2)=[CH:21][CH:22]=1>C(O)CCC>[CH3:28][N:26]1[CH:27]=[C:23]([C:20]2[CH:21]=[CH:22][C:17]3[N:14]([C:12]([CH2:11][C:7]4[CH:6]=[C:5]5[C:10](=[CH:9][CH:8]=4)[N:1]=[CH:2][N:3]=[CH:4]5)=[N:19][N:18]=3)[N:15]=2)[CH:24]=[N:25]1

Participants

4

Reactant 2

HCID 545956073-Chloro-6-(1-methyl-1H-pyrazol-4-yl)pyridazineHCID 57654572HCID 57654572, compound

Product 1

HCID 57654475HCID 57654475, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Quinazolin-6-yl-acetic acid hydrazide (0.032 g, 0.158 mmol) and 3-chloro-6-(1-methyl-1H-pyrazol-4-yl)-pyridazine (0.031 g, 0.158 mmol) were heated to 165° C. in butanol (2 mL) for five hours. The reaction was cooled to room temperature, evaporated in vacuo and purified via silica gel column chromatography eluting with 5% methanol in dichloromethane to give 0.0031 g (7%) of 6-[6-(1-methyl-1H -pyrazol-4-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl]-quinazoline. 1H NMR (400 MHz, CD3OD) δ 8.45 (s, 1H), 8.29 (s, 1H), 8.06 (d, 2H, J=9.6 Hz), 7.60 (d, 2H, J=9.6 Hz), 7.55 (m, 1H), 7.17 (d, 1H, J=8.0 Hz), 6.08 (s, 1H), 4.58 (m, 2H), 3.89 (s, 3H). Mass spectrum (LCMS, ESI pos.): Calcd for C18H14N8; found: 343.3 (M+H).

Workup

  1. customevaporated in vacuo
  2. custompurified via silica gel column chromatography
  3. washeluting with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-dda9b6f596ac44fb8c42e081ca6c5fd1
Source dataset
uspto-grants-2011_10
Patent number
US08030305B2

Reaction notes

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