Water → HCID 58955249, compound

HRID 1921609Notes

Reaction equation

HRID 1921609 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]=[CH: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.O>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][CH:3]=[CH:4]5)=[N:19][N:18]=3)[N:15]=2)[CH:24]=[N:25]1

Participants

5

Reactant 3

HCID 962WaterHCID 39733754HCID 39733754, compoundHCID 545956073-Chloro-6-(1-methyl-1H-pyrazol-4-yl)pyridazine

Product 1

HCID 58955249HCID 58955249, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

Quinolin-6-yl-acetic acid hydrazide (188 mg, 0.93 mmol) and 3-Chloro-6-(1-methyl-1H-pyrazol-4-yl)-pyridazine (202 mg, 0.93 mmol, Example 1: step a) were dissolved in butanol (120 mL). The reaction mixture was heated to 120° C. overnight fitted with water cooled refluxing condenser and argon line. The reaction was concentrated in vacuo followed by HPLC purification (5-65% CH3CN over 40 min) resulting in the title compound as a tan solid (201.6 mg, 65%). 1H-NMR (CD3OD): δ 9.08-9.04 (2H, m), 8.30-8.29 (2H, m), 8.21-8.06 (4H, m), 7.99-7.95 (1H, q, J=5.3, 3.0 Hz), 7.68-7.65 (1H, d, J=9.8), 4.85 (2H, s), 3.89 (3H, s), 4.96 (2H, s). ESI-MS (m/z): Calcd. For C19H15N7: 341.37; found: 342.3 (M+H).

Workup

  1. temperaturecooled
  2. temperaturerefluxing condenser
  3. concentrationThe reaction was concentrated in vacuo
  4. customfollowed by HPLC purification (5-65% CH3CN over 40 min)

Sources & evidence

ORD record
ord-173dbb870ffb4db995399627ec0fdedc
Source dataset
uspto-grants-2012_05
Patent number
US08173654B2

Reaction notes

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