Acetic Acid → 1-{[2-(2-Fluorophenyl)-3-oxo-2,3-dihydropyrazolo[4,3-c]quinolizin-5-yl]methyl}-4-(4-methylpyridin-2-yl)piperidine-4-carbonitrile

HRID 1890811Notes

Reaction equation

HRID 1890811 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:22](=[O:23])[C:11]2=[CH:12][C:13]([CH:20]=O)=[C:14]3[N:19]([C:10]2=[N:9]1)[CH:18]=[CH:17][CH:16]=[CH:15]3.[CH3:24][C:25]1[CH:30]=[CH:29][N:28]=[C:27]([C:31]2([C:37]#[N:38])[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)[CH:26]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCCl.C(#N)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:22](=[O:23])[C:11]2=[CH:12][C:13]([CH2:20][N:34]3[CH2:35][CH2:36][C:31]([C:27]4[CH:26]=[C:25]([CH3:24])[CH:30]=[CH:29][N:28]=4)([C:37]#[N:38])[CH2:32][CH2:33]3)=[C:14]3[N:19]([C:10]2=[N:9]1)[CH:18]=[CH:17][CH:16]=[CH:15]3

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 533632764-(4-Methylpyridin-2-yl)piperidine-4-carbonitrileHCID 867620072-(2-Fluorophenyl)-3-oxo-2,3-dihydropyrazolo[4,3-c]quinolizine-5-carbaldehyde

Product 1

HCID 534821421-{[2-(2-Fluorophenyl)-3-oxo-2,3-dihydropyrazolo[4,3-c]quinolizin-5-yl]methyl}-4-(4-methylpyridin-2-yl)piperidine-4-carbonitrile

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6342AcetonitrileSolvent

Procedure

2-(2-Fluorophenyl)-3-oxo-2,3-dihydropyrazolo[4,3-c]quinolizine-5-carbaldehyde (0.025 g, 0.081 mmol) was suspended in a mixture of 1,2-dichloroethane (2 mL) and acetonitrile (4 mL) containing powdered 4 Å molecular sieves and treated with 4-(4-methylpyridin-2-yl)piperidine-4-carbonitrile (0.018 g, 0.094 mmol. 1.2 equiv), acetic acid (0.028 mL, 0.49 mmol, 6.0 equiv), and sodium triacetoxyborohydride (0.034 g, 0.16 mmol, 2.0 equiv). After stirring at ambient temperature for 60 hours, the mixture was poured into saturated aqueous sodium bicarbonate and extracted with dichloromethane (2×).

Workup

  1. additioncontaining
  2. extractionextracted with dichloromethane (2×)

Sources & evidence

ORD record
ord-36e57b1be5924defb92d4a4661c87b0e
Source dataset
uspto-grants-2013_08
Patent number
US08507494B2

Reaction notes

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