Methylhydrazine → 6-methyl-2-{[4-(4-methylpiperazin-1-yl)phenyl]amino}-8-phenylpyrimido[4,5-d]pyridazin-5(6H)-one

HRID 2402945Notes

Reaction equation

HRID 2402945 reaction equation
[C:1]([C:9]1[C:14]([C:15]([O:17]CC)=O)=[CH:13][N:12]=[C:11]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([N:27]3[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]3)=[CH:23][CH:22]=2)[N:10]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:34][NH:35][NH2:36]>C(O)CCC>[CH3:34][N:35]1[C:15](=[O:17])[C:14]2[CH:13]=[N:12][C:11]([NH:20][C:21]3[CH:22]=[CH:23][C:24]([N:27]4[CH2:28][CH2:29][N:30]([CH3:33])[CH2:31][CH2:32]4)=[CH:25][CH:26]=3)=[N:10][C:9]=2[C:1]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[N:36]1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 71224273HCID 71224273, compound

Product 1

HCID 712240066-methyl-2-{[4-(4-methylpiperazin-1-yl)phenyl]amino}-8-phenylpyrimido[4,5-d]pyridazin-5(6H)-one

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of Example 3B (50 mg, 0.112 mmol) and methylhydrazine (6.50 μl, 0.123 mmol) in n-butanol (12.5 mL) was heated to 170° C. by microwave irradiation (Biotage Initiator) for 3 hour. The reaction mixture was cooled to room temperature, and the solid was filtered and air-dried to provide the title compound. MS ESI(+) m/z 428.2 [M+H]+; 1H NMR (300 MHz, DMSO-d6): δ ppm 10.34 (s, 1H), 9.29 (s, 1H), 7.94-7.91 (m, 2H), 7.59-7.48 (m, 5H), 6.84 (d, J=8.7 Hz, 2H), 3.75 (s, 3H), 3.13-3.05 (m, 4H), 2.47-2.44 (m, 4H), 2.22 (s, 3H).

Workup

  1. filtrationthe solid was filtered
  2. customair-dried

Sources & evidence

ORD record
ord-1a47ad3b13ff41b4a1cf9781ecd63ca3
Source dataset
uspto-grants-2014_08
Patent number
US08796289B2

Reaction notes

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