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Triphenylphosphine → 4-chloro-3-(1-methyl-1H-pyrazol-4-yl)-1-(2-(4-methylpiperazin-1-yl)ethyl)-5-phenyl-1H-pyrazolo[3,4-c]pyridazine

HRID 588563
Notes
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Reaction equation

HRID 588563 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[NH:14][N:15]=[C:16](I)[C:3]=12.ClC1C(C2C=CC=CC=2)=NN=[C:21]2[NH:31][N:32]=[CH:33][C:20]=12.[CH3:34][N:35]1[CH2:40][CH2:39][N:38]([CH2:41][CH2:42]O)[CH2:37][CH2:36]1.N(C(OCC)=O)=N[C:46](OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCOCC1>[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]([CH2:42][CH2:41][N:38]3[CH2:39][CH2:40][N:35]([CH3:34])[CH2:36][CH2:37]3)[N:15]=[C:16]([C:20]3[CH:21]=[N:31][N:32]([CH3:46])[CH:33]=3)[C:3]=12
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2311841-(2-Hydroxyethyl)-4-methylpiperazineHCID 867172634-chloro-5-phenyl-1H-pyrazolo[3,4-c]pyridazineHCID 86717264CID 86717264

Product 1

HCID 74220953
4-chloro-3-(1-methyl-1H-pyrazol-4-yl)-1-(2-(4-methylpiperazin-1-yl)ethyl)-5-phenyl-1H-pyrazolo[3,4-c]pyridazine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 4-chloro-3-iodo-5-phenyl-1H-pyrazolo[3,4-c]pyridazine and 4-chloro-5-phenyl-1H-pyrazolo[3,4-c]pyridazine (9:1, 1.4 g), 2-(4-methylpiperazin-1-yl)ethanol (1.13 g, 7.8 mmol), diethyl azodicarboxylate (1.37 g, 7.8 mmol) and triphenyl phosphine (2.07 g, 7.9 mmol) in 1,4-dioxane (26 mL) was heated to 85° C. for 1 h and then cooled to room temperature and concentrated in vacuo. The residue was partially purified by column chromatography (silica gel, starting with iso-hexanes/ethyl acetate 1:0 to 0:1 and finishing with ethyl acetate/4 M NH3 in MeOH 1:0 to 9:1). The residue was purified by preparative HPLC to provide Compounds Ia, Ib, and 20.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partially purified by column chromatography (silica gel, starting with iso-hexanes/ethyl acetate 1:0 to 0:1 and finishing with ethyl acetate/4 M NH3 in MeOH 1:0 to 9:1)
  3. customThe residue was purified by preparative HPLC
  4. customto provide Compounds Ia, Ib, and 20

Sources & evidence

ORD record
ord-a1e2d75a23b14d10a89a5c9a8ca82ca6
Source dataset
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09227976B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes