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

HRID 714400Notes

Reaction equation

HRID 714400 reaction equation
F[C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[F:25])[CH2:5][N:6]1[CH2:10][CH2:9][N:8]([C:11]2[CH:12]=[C:13]([CH:18]=[CH:19][N:20]=2)[C:14]([O:16]C)=O)[C:7]1=[O:21].[C-:26]#[N:27].[Na+]>N1C=CC=CC=1CN>[CH2:26]([NH:27][C:14](=[O:16])[C:13]1[CH:18]=[CH:19][N:20]=[C:11]([N:8]2[CH2:9][CH2:10][N:6]([CH2:5][C:4]3[CH:22]=[CH:23][C:24]([F:25])=[CH:2][CH:3]=3)[C:7]2=[O:21])[CH:12]=1)[C:2]1[CH:3]=[CH:4][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 58247785Methyl 2-(3-(3,4-difluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinate

Product 1

HCID 44552918N-benzyl-2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-isonicotinamideYield 116.8%

Reagents, catalysts & solvents 1

HCID 195092-PyridinemethanamineSolvent

Procedure

A solution of methyl 2-(3-(3,4-difluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinate (0.25 g, 0.72 mmol) and sodium cyanide (0.10 g, 2.04 mmol) in pyridin-2-ylmethanamine (3.0 mL) was stirred at 95° C. for 16 hours and concentrated in vacuo. The residue was purified by column chromatography eluted with 0 to 90% of ethyl acetate in dichloromethane to give N-benzyl-2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-isonicotinamide as a colorless solid (0.17 g, yield 54%): mp 99-101° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.74 (t, J=6.0 Hz, 1H), 8.62 (s, 1H), 8.49-8.47 (m, 1H), 8.39 (d, J=5.1 Hz, 1H), 7.76-7.70 (m, 1H), 7.44-7.22 (m, 5H), 7.19-7.15 (m, 1H), 4.54 (d, J=6.0 Hz, 2H), 4.39 (s, 2H), 3.96 (t, J=8.1 Hz, 2H), 3.38 (t, J=8.1 Hz, 2H); MS (ES+) m/z 423.8 (M+1).

Workup

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

Sources & evidence

ORD record
ord-a3e89a41a5e748c082669f37891c95a8
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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