4-Benzyloxybenzoylchloride → HCID 44128288, compound

HRID 2167335Notes

Reaction equation

HRID 2167335 reaction equation
[OH:1]/[N:2]=[C:3](\[NH2:17])/[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[CH:6][CH:5]=1.[CH2:18]([O:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=O)=[CH:28][CH:27]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>N1C=CC=CC=1>[CH2:18]([O:25][C:26]1[CH:27]=[CH:28][C:29]([C:30]2[O:1][N:2]=[C:3]([C:4]3[CH:5]=[CH:6][C:7]([O:10][C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=4)=[CH:8][CH:9]=3)[N:17]=2)=[CH:33][CH:34]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 37664104-BenzyloxybenzoylchlorideHCID 59533941HCID 59533941, compound

Product 1

HCID 44128288HCID 44128288, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(Z)-N′-Hydroxy-4-(pyridin-2-yloxy)benzamidine (339 mg, 137 μmol) and 4-benzyloxybenzoyl chloride (24 mg, 106 μmol) were suspended in pyridine (2.0 mL) the solution was refluxed for 21 hours. The reaction mixture was then cooled to room temperature and solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (Hex/EtOAc 2:1) to give the product as a white solid (20 mg, 46%). 1H NMR (500 MHz, CDCL3) δ(ppm): 5.16 (2H, s), 6.99 (1H, d, J=8.2 Hz), 7.05 (1H, ddd, J=7.2, 5.0, 0.80 Hz), 7.11 (2H, d, J=8.8 Hz), 7.27 (2H, d, J=8.8 Hz), 7.34-7.38 (1H, m), 7.40-7.46 (4H, m), 7.73 (1H, ddd, J=8.8, 8.2, 2.0 Hz), 8.16 (2H, d, J=9.0 Hz), 8.20 (2H, d, J=8.6 Hz), 8.24 (1H, dd, J=5.0, 2.0Hz). 13C NMR (125 MHz, CDCL3) δ(ppm): 70.4 (CH2), 112.3 (CH), 115.5 (CH), 117.3, 119.3 (CH), 121.4 (CH), 123.5, 127.7 (CH), 128.5 (CH), 128.9 (CH), 129.3 (CH), 130.3 (CH), 136.2, 139.9 (CH), 148.0 (CH), 156.8, 162.5, 163.3, 168.5, 175.7. MS (FAB+): 422 (MH+). HRMS for C26H19N3O3 (MH+): calculated: 422.1505; found 422.1505.

Workup

  1. temperaturewas refluxed for 21 hours
  2. customsolvent was removed under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (Hex/EtOAc 2:1)

Sources & evidence

ORD record
ord-ab1198e0b6304ba487edb2cf4422cbd1
Source dataset
uspto-grants-2015_06
Patent number
US09045442B2

Reaction notes

Loading…