Piperidine → HCID 21106538, compound

HRID 1783689Notes

Reaction equation

HRID 1783689 reaction equation
[C:1]([N:5]1[C:9]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14](=[O:21])[N:13]([C:22]3[CH:27]=[CH:26][C:25](Cl)=[CH:24][CH:23]=3)[N:12]=2)=[CH:8][C:7]([CH3:29])=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[NH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1.CC([O-])(C)C.[Na+].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:1]([N:5]1[C:9]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14](=[O:21])[N:13]([C:22]3[CH:27]=[CH:26][C:25]([N:30]4[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]4)=[CH:24][CH:23]=3)[N:12]=2)=[CH:8][C:7]([CH3:29])=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 8082PiperidineHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 21106537HCID 21106537, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 21106538HCID 21106538, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

4-(2-tert-Butyl-5-methyl-2H-pyrazol-3-ylamino)-2-(4-chlorophenyl)-2H-phthalazin-1-one (0.10 g, 0.25 mmol), piperidine (0.025 g, 0.29 mmol), NaOtBu (0.033 g, 0.34 mmol), tris-(dibenzylideneacetone)-dipalladium (0.06 g, 0.008 mmol) and 2-(di-t-butylphosphino)-biphenyl (0.004 g, 0.014 mmol) under argon were heated to 100° C. for 19 hours, and then allowed to cool to RT. The solvent was evaporated in vacuum, the residue was diluted in H2O (30 ml) and the resulting solid was collected by filtration. Purification of the raw product by preparative HPLC gave the title compound (0.014 g, 13% yield). 1H-NMR: (400 MHz, D6-DMSO) 8.35 (1H, d), superimposed by 8.34 (1H, s), 8.29 (1H, d), 8.01 (1H, t), 7.92 (1H, t), 7.31 (2H, d), 6.92 (2H, d), 5.94 (1H, s), 3.16 (4H, m), 1.61 (4H, m), 1.55 (9H, s), superimposes 1.54 (2H, m); MS (ESI+)=457.16 (M+H)+.

Workup

  1. customThe solvent was evaporated in vacuum
  2. additionthe residue was diluted in H2O (30 ml)
  3. filtrationthe resulting solid was collected by filtration
  4. customPurification of the raw product by preparative HPLC

Sources & evidence

ORD record
ord-7a1b197c94924105a72dc888b7eebf3f
Source dataset
uspto-grants-2009_03
Patent number
US07501410B2

Reaction notes

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