Selectfluor → HCID 57635828, compound

HRID 2109949Notes

Reaction equation

HRID 2109949 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]2[C:12]([C:17]([OH:19])=[O:18])=[N:13][CH:14]=[CH:15][CH:16]=2)[N:7]([C:20]2[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:27])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[F:28][B-](F)(F)F.F[B-](F)(F)F.ClC[N+]12CC[N+](F)(CC1)CC2>CC#N>[C:1]([C:5]1[C:9]([F:28])=[C:8]([NH:10][C:11]2[C:12]([C:17]([OH:19])=[O:18])=[N:13][CH:14]=[CH:15][CH:16]=2)[N:7]([C:20]2[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:27])[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 2724933Selectfluor2×HCID 11257045HCID 11257045, compound

Product 1

HCID 57635828HCID 57635828, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-{[3-tert-butyl-1-(2,6-dimethylphenyl)-1H-pyrazol-5-yl]amino}pyridine-2-carboxylic acid (Example 10, 50 mg, 0.14 mmol) in CH3CN (1 mL) was added [(1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)] (SELECTFLUOR™) (48 mg, 0.14 mmol), and the mixture was stirred at rt for 16 h. The mixture was concentrated, and the residue was subjected to HPLC purification with a gradient elution from 10% to 90% acetonitrile in water to afford 22 mg (42%) of the title compound. 1H NMR (300 MHz, CD2Cl2) δ 9.18 (s, 1H), 8.04 (d, 1H), 7.50 (dd, 1H), 7.42 (m, 1H), 7.28 (m, 1H), 7.13 (m, 2H), 2.12 (s, 6H), 1.40 (s, 9H). ES-MS m/z 383.1 (MH+); HPLC RT (min) 3.21.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was subjected to HPLC purification with a gradient elution from 10% to 90% acetonitrile in water

Sources & evidence

ORD record
ord-e0481d6a59a3453f8e63bc01915c2889
Source dataset
uspto-grants-2009_04
Patent number
US07517878B2

Reaction notes

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