Potassium Fluoride → HCID 53374176, compound

HRID 869696Notes

Reaction equation

HRID 869696 reaction equation
CS(O[C@H:6]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[C:15]([NH:17][CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[N:14]3[N:24]=[C:25]([C:27]4[C:36]([CH3:37])=[N:35][C:34]5[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=5)[N:28]=4)[CH:26]=[C:13]3[N:12]=2)[CH2:7]1)(=O)=O.[F-].[K+]>C(#N)C>[N:8]1([C:11]2[CH:16]=[C:15]([NH:17][CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[N:14]3[N:24]=[C:25]([C:27]4[C:36]([CH3:37])=[N:35][C:34]5[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=5)[N:28]=4)[CH:26]=[C:13]3[N:12]=2)[CH2:7][CH:6]=[CH:10][CH2:9]1

Participants

4

Reactant 2

HCID 522689Potassium FluorideHCID 86674512HCID 86674512, compound

Product 1

HCID 53374176HCID 53374176, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (35)-1-[2-(3-methylquinoxalin-2-yl)-7-(tetrahydro-2H-pyran-4-ylamino)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-3-yl methanesulfonate (50 mg, 0.0955 mmol) 4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane (108 mg, 0.286 mmol), and potassium fluoride (17 mg, 0.286 mmol) in acetonitrile (2.0 mL) was refluxed for 15 min. After being cooled to ambient temperature, the reaction mixture was concentrated in vacuo. The crude was purified by silica gel column chromatography (chloroform to chloroform:methanol=97:3) to give 5-(2,5-dihydro-1H-pyrrol-1-yl)-2-(3-methylquinoxalin-2-yl)-N-(tetrahydro-2H-pyran-4-yl)pyrazolo[1,5-a]pyrimidin-7-amine (the compound of Example 1.009 listed in the Table of Examples as described hereinafter). 1H-NMR (400 MHz, CDCl3): δ 1.73-1.82 (2H, m), 2.13-2.16 (2H, m), 3.04 (3H, s), 3.59 (2H, dt, J=11.8, 2.1 Hz), 3.68-3.78 (1H, m), 4.09 (2H, dt, J=11.8, 3.6 Hz), 4.38 (4H, br), 5.17 (1H, s), 5.98 (2H, s), 6.17 (1H, d, J=7.9 Hz), 6.67 (1H, s), 7.69-7.77 (2H, m), 8.03-8.06 (1H, m), 8.17-8.19 (1H, m).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customThe crude was purified by silica gel column chromatography (chloroform to chloroform:methanol=97:3)

Sources & evidence

ORD record
ord-b108c0303ea44cce92da960420747dde
Source dataset
uspto-grants-2015_03
Patent number
US08969376B2

Reaction notes

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