Triphenylphosphine → 3-(1-{3-[5-(4-Methylpiperazin-1-yl)pyrimidin-2-yl]benzyl}-6-oxo-1,6-dihydropyridazin-3-yl)benzonitrile

HRID 925484Notes

Reaction equation

HRID 925484 reaction equation
[O:1]=[C:2]1[NH:7][N:6]=[C:5]([C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[C:11]#[N:12])[CH:4]=[CH:3]1.[CH3:16][N:17]1[CH2:22][CH2:21][N:20]([C:23]2[CH:24]=[N:25][C:26]([C:29]3[CH:30]=[C:31]([CH2:35]O)[CH:32]=[CH:33][CH:34]=3)=[N:27][CH:28]=2)[CH2:19][CH2:18]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>CN(C=O)C>[CH3:16][N:17]1[CH2:18][CH2:19][N:20]([C:23]2[CH:28]=[N:27][C:26]([C:29]3[CH:30]=[C:31]([CH:32]=[CH:33][CH:34]=3)[CH2:35][N:7]3[C:2](=[O:1])[CH:3]=[CH:4][C:5]([C:8]4[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=4)[C:11]#[N:12])=[N:6]3)=[N:25][CH:24]=2)[CH2:21][CH2:22]1

Participants

6

Reactant 4

HCID 11776Triphenylphosphine2×HCID 97268Di-tert-butyl azodicarboxylate2×HCID 203265203-(6-Oxo-1,6-dihydropyridazin-3-yl)benzonitrileHCID 59484860{3-[5-(4-Methylpiperazin-1-yl)pyrimidin-2-yl]phenyl}methanol

Product 1

HCID 594849053-(1-{3-[5-(4-Methylpiperazin-1-yl)pyrimidin-2-yl]benzyl}-6-oxo-1,6-dihydropyridazin-3-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

149 mg (0.76 mmol) of 3-(6-oxo-1,6-dihydropyridazin-3-yl)benzonitrile and 256 mg (0.76 mmol) of {3-[5-(4-methylpiperazin-1-yl)pyrimidin-2-yl]phenyl}-methanol are suspended in 5 ml of DMF with 378 mg (1.13 mmol) of polymer-bound triphenylphosphine (about 3 mmol of triphenylphosphine per g) and shaken at room temperature for 30 min. 266 mg (1.134 mmol) of di-tert-butyl azodicarboxylate are added. The reaction mixture is shaken at room temperature for 2 h. A further 378 mg (1.13 mmol) of polymer-bound triphenylphosphine (about 3 mmol of triphenylphosphine per g) and 266 mg (1.134 mmol) of di-tert-butyl azodicarboxylate are added, and the reaction mixture is shaken at room temperature for 2 h. The reaction mixture is filtered, the filtrate is evaporated, and the residue is purified by means of column chromatography on silica gel; yield: 59 mg of “A287”; HPLC: Rt=2.38 min (method C); LC-MS: 464 (M+H).

Workup

  1. stirringThe reaction mixture is shaken at room temperature for 2 h
  2. stirringthe reaction mixture is shaken at room temperature for 2 h
  3. filtrationThe reaction mixture is filtered
  4. customthe filtrate is evaporated
  5. customthe residue is purified by means of column chromatography on silica gel

Sources & evidence

ORD record
ord-12370241aba8492eba2a0f814ef79d72
Source dataset
uspto-grants-2016_03
Patent number
US09284300B2

Reaction notes

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