HCID 54724162, compound → HCID 22050728, compound

HRID 1867019Notes

Reaction equation

HRID 1867019 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][N:6]1[CH:11]=[CH:10][C:9](O)=[CH:8][C:7]1=[O:13]>C(N)C1C=CC=CC=1>[CH2:5]([NH:6][C:9]1[CH:10]=[CH:11][N:6]([CH2:5][C:4]2[CH:14]=[CH:15][CH:16]=[C:2]([F:1])[CH:3]=2)[C:7](=[O:13])[CH:8]=1)[C:4]1[CH:14]=[CH:15][CH:16]=[CH:2][CH:3]=1

Participants

3

Reactant 1

HCID 54724162HCID 54724162, compound

Product 1

HCID 22050728HCID 22050728, compound

Reagents, catalysts & solvents 1

HCID 7504BenzylamineSolvent

Conditions

Temperature
185 °C

Procedure

A mixture of 1-(3-fluorobenzyl)-4-hydroxypyridin-2(1H)-one (1.005 g, 4.5 mmol) in benzylamine (15 mL) was heated at reflux (185° C.) under nitrogen atmosphere for 24 hours. The reaction was monitored by ES-MS (MH+ 309). The solvent was removed by vacuum distillation to give a yellow residue. 1H-NMR (CD3OD, 400 MHz) δ7.31 (m, 7H), 7.03 (m, 3H), 5.98 (d, 1H, J=7.2 Hz), 5.45 (s, 1H), 5.00 (s, 2H), 4.30 (s, 2H); ES-HRMS m/z 309.1403 (M+H calculated for C19H18N2OF requires 309.1375).

Workup

  1. temperaturewas heated
  2. customThe solvent was removed by vacuum distillation
  3. customto give a yellow residue

Sources & evidence

ORD record
ord-2757146beb82457f8de527b2d1d2c949
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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