(4-Fluorobenzyl)isobutylamine → Imidazole-1-sulfonic acid (4-fluoro-benzyl)-isobutyl-amide

HRID 1403711Notes

Reaction equation

HRID 1403711 reaction equation
[F:1][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][NH:7][CH2:8][CH:9]([CH3:11])[CH3:10])=[CH:4][CH:3]=1.[O-]S(C(F)(F)F)(=O)=O.[N:22]1([S:27](N2C=C[N+](C)=C2)(=[O:29])=[O:28])[CH:26]=[CH:25][N:24]=[CH:23]1>CC#N>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]([CH2:8][CH:9]([CH3:11])[CH3:10])[S:27]([N:22]2[CH:26]=[CH:25][N:24]=[CH:23]2)(=[O:29])=[O:28])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 966924(4-Fluorobenzyl)isobutylamineHCID 117281493-(Imidazole-1-sulfonyl)-1-methyl-3H-imidazol-1-ium triflate

Product 1

HCID 90437309Imidazole-1-sulfonic acid (4-fluoro-benzyl)-isobutyl-amideYield 32%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (4-fluoro-benzyl)-isobutyl-amine (500 mg, 2.76 mmol) in MeCN (20 mL) was treated with 3-(imidazole-1-sulfonyl)-1-methyl-3H-imidazol-1-ium triflate (1.49 g, 4.14 mmol) and heated at reflux for 18 hours. The cooled reaction mixture was concentrated under vacuum and purified by silica gel chromatography (0-50% EtOAc in DCM) to afford the title compound (275 mg, 32%) as a pale yellow oil. 1H NMR (300 MHz, CDCl3) δ 7.95 (s, 1H), 7.17 (m, 4H), 7.02 (m, 2H), 4.40 (s, 2H), 3.01 (d, J=7.6 Hz, 2H), 1.77 (m, 1H), 0.80 (d, J=6.6 Hz, 6 H). LCMS (m/z, Method A) ES+ 312.0 [M+1]+.

Workup

  1. temperatureheated
  2. temperatureat reflux for 18 hours
  3. customThe cooled reaction mixture
  4. concentrationwas concentrated under vacuum
  5. custompurified by silica gel chromatography (0-50% EtOAc in DCM)

Sources & evidence

ORD record
ord-6914e33c9a074759bc756e18a4d4ef53
Source dataset
uspto-grants-2014_12
Patent number
US08912219B2

Reaction notes

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