Sodium Cyanide → N-benzyl-2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-isonicotinamide

HRID 714369Notes

Reaction equation

HRID 714369 reaction equation
[F:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2[CH2:11][CH2:10][N:9]([C:12]3[CH:13]=[C:14]([CH:19]=[CH:20][N:21]=3)[C:15](OC)=[O:16])[C:8]2=[O:22])=[CH:4][CH:3]=1.[C-:25]#[N:26].[Na+]>C(N)C1C=CC=CC=1>[CH2:25]([NH:26][C:15](=[O:16])[C:14]1[CH:19]=[CH:20][N:21]=[C:12]([N:9]2[CH2:10][CH2:11][N:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:24][CH:23]=3)[C:8]2=[O:22])[CH:13]=1)[C:2]1[CH:24]=[CH:23][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 58247772Methyl 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinate

Product 1

HCID 44552918N-benzyl-2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-isonicotinamideYield 120.5%

Reagents, catalysts & solvents 1

HCID 7504BenzylamineSolvent

Procedure

A solution of methyl 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinate (0.26 g, 0.78 mmol) and sodium cyanide (78 mg, 1.56 mmol) in benzylamine (5.0 mL) was stirred at 95° C. for 16 hours and concentrated in vacuo. The residue was purified by column chromatography eluting with 0 to 90% of ethyl acetate in hexanes to give N-benzyl-2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinamide as a colorless solid (0.19 g, yield 59%): mp 167-169° C.; 1H NMR (300 MHz, CDCl3) δ 8.57 (d, J=0.6 Hz, 1H), 8.37 (d, J=5.1 Hz, 1H), 7.42-7.18 (m, 8H), 7.08-6.98 (m, 2H), 6.79 (br s, 1H), 4.62 (d, J=6.0 Hz, 2H), 4.41 (s, 2H), 4.03 (t, J=7.5 Hz, 2H), 3.36 (t, J=7.8 Hz, 2H); 13C NMR (75 MHz, CDCl3) δ 165.7, 164.0, 160.7, 157.0, 153.0, 148.4, 143.0, 137.7, 132.1, 132.0, 129.9, 129.8, 128.8, 128.0, 127.7, 116.1, 115.8, 115.6, 109.0, 47.2, 44.2, 41.3, 41.0; MS (ES+) m/z 405.2 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by column chromatography
  3. washeluting with 0 to 90% of ethyl acetate in hexanes

Sources & evidence

ORD record
ord-58bc237e5de54a4f9651183ddac4752d
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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