4-(2-hydrazinylethyl)morpholine → 4-(2-(4-chloro-3,5-diphenyl-1H-pyrazolo[3,4-c]pyridazin-1-yl)ethyl)morpholine

HRID 1775544Notes

Reaction equation

HRID 1775544 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:6][N:5]=[C:4]2[N:14]([CH2:23][CH3:24])[N:15]=[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:3]=12.N(CC[N:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1)N>>[Cl:1][C:2]1[C:7]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[N:6][N:5]=[C:4]2[N:14]([CH2:23][CH2:24][N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)[N:15]=[C:16]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:3]=12

Participants

3

Reactant 2

HCID 30293944-(2-hydrazinylethyl)morpholineHCID 665768074-Chloro-1-ethyl-3,5-diphenyl-1H-pyrazolo[3,4-c]pyridazine

Product 1

HCID 665769654-(2-(4-chloro-3,5-diphenyl-1H-pyrazolo[3,4-c]pyridazin-1-yl)ethyl)morpholine

Procedure

Compound 28 was synthesised following similar procedures outlined in Example 31 (Compound 18), using 4-(2-hydrazinylethyl)morpholine instead of ethyl hydrazine in Step 3. As a slightly modified procedure, Step 3 was performed at 60° C. for 16 h. The reaction mixture was concentrated in vacuo and the crude residue was purified by column chromatography (silica gel, gradient 50 to 100% ethyl acetate/isohexane), followed by preparative HPLC, yielding Compound 28 as a solid.

Workup

  1. customCompound 28 was synthesised
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe crude residue was purified by column chromatography (silica gel, gradient 50 to 100% ethyl acetate/isohexane)

Sources & evidence

ORD record
ord-e8a6f46f5f7746488757590b7afb1b55
Source dataset
uspto-grants-2016_02
Patent number
US09260381B2

Reaction notes

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