Triethylamine → (R)-(3-methyl-4-(1-phenylpyrido[3,4-d]pyridazin-4-yl)piperazin-1-yl)(morpholino)methanone

HRID 1514376Notes

Reaction equation

HRID 1514376 reaction equation
[CH3:1][C@@H:2]1[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[C:8]1[N:9]=[N:10][C:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=12.C(N(CC)CC)C.[N:31]1([C:37](Cl)=[O:38])[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1>C(Cl)Cl.CCOC(C)=O>[CH3:1][C@H:2]1[N:3]([C:8]2[N:9]=[N:10][C:11]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[C:12]3[CH:17]=[CH:16][N:15]=[CH:14][C:13]=23)[CH2:4][CH2:5][N:6]([C:37]([N:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)=[O:38])[CH2:7]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 848104-Morpholinecarbonyl chlorideHCID 57657605(R)-4-(2-methylpiperazin-1-yl)-1-phenylpyrido[3,4-d]pyridazine

Product 1

HCID 25226949(R)-(3-methyl-4-(1-phenylpyrido[3,4-d]pyridazin-4-yl)piperazin-1-yl)(morpholino)methanone

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)-4-(2-methylpiperazin-1-yl)-1-phenylpyrido[3,4-d]pyridazine 16 (105 mg, 344 μmol) in 5 mL of CH2Cl2 was added triethylamine (96 μl, 688 μmol) followed by 4-morpholinylcarbonyl chloride (55 μl, 413 μmol). After 4 h, the reaction was diluted with 60 mL of EtOAc and washed with sat. NaHCO3 and brine. The organic layer was dried over MgSO4, filtered, and concentrated. Purification by column chromatography afforded (R)-(3-methyl-4-(1-phenylpyrido[3,4-d]pyridazin-4-yl)piperazin-1-yl)(morpholino)methanone 36. MS 418.2 (calc'd) 419.2 (M+H, found).

Workup

  1. washwashed with sat. NaHCO3 and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by column chromatography

Sources & evidence

ORD record
ord-d4dbc1636e954ccc973f5dc318061c8f
Source dataset
uspto-grants-2012_07
Patent number
US08222251B2

Reaction notes

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