Tetrabutylammonium Fluoride → HCID 178505076, compound

HRID 1875239Notes

Reaction equation

HRID 1875239 reaction equation
[CH3:1][S:2]([N:5](S(C)(=O)=O)[C:6]1[NH:7][C:8]([C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([O:23][C:24]3[CH:29]=[C:28]([C:30]#[N:31])[CH:27]=[C:26]([Cl:32])[CH:25]=3)[C:17]=2[F:33])=[O:13])=[C:9]([Cl:11])[N:10]=1)(=[O:4])=[O:3].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Cl:11][C:9]1[N:10]=[C:6]([NH:5][S:2]([CH3:1])(=[O:3])=[O:4])[NH:7][C:8]=1[C:12]([NH:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([O:23][C:24]2[CH:29]=[C:28]([C:30]#[N:31])[CH:27]=[C:26]([Cl:32])[CH:25]=2)[C:17]=1[F:33])=[O:13]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium Fluoride2×HCID 178505077HCID 178505077, compound

Product 1

HCID 178505076HCID 178505076, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-[bis(methylsulfonyl)amino]-4-chloro-N-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-1H-imidazole-5-carboxamide (0.030 g, 0.049 mmol) and TBAF (0.059 mL of a 1M solution in THF, 0.059 mmol) in THF (0.5 mL) was heated overnight under reflux. Additional TBAF (0.050 mL, 0.050 mmol) was added and stirring was continued at RT for 3 days. The solution was concentrated and purified by Reverse-Phase HPLC (water:acetonitrile with 0.1% TFA) to provide the title compound (0.012 g, 46%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.79 (br. s., 1H) 10.64 (br. s., 1H) 8.35 (br. s., 1H) 7.83 (s, 1H) 7.44-7.55 (m, 3H) 7.39 (t, J=6.59 Hz, 1H) 4.51 (br. s., 2H) 3.20 (br. s., 3H). ES-LCMS: m/z 532.1, 534.1, 536.0 (M+1).

Workup

  1. temperatureunder reflux
  2. concentrationThe solution was concentrated
  3. custompurified by Reverse-Phase HPLC (water:acetonitrile with 0.1% TFA)

Sources & evidence

ORD record
ord-057d6333750b42c79e52da730211ebf4
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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