4-Benzyloxybenzoylchloride → HCID 59533951, compound

HRID 2167343Notes

Reaction equation

HRID 2167343 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][N:14]=[CH:13][CH: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][N:14]=[CH:13][CH: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 59533948HCID 59533948, compound

Product 1

HCID 59533951HCID 59533951, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(Z)-N′-Hydroxy-4-(pyridin-4-yloxy)benzamidine (20 mg, 88 μmol) and 4-benzyloxybenzoyl chloride (28 mg, 114 μmol) were suspended in pyridine (5.0 mL). The solution was refluxed for 21 hours, cooled to room temperature and the solvent was removed under reduced pressure. The solid residue was purified by silica gel column chromatography to give the product as a white solid (10 mg, 27%). 1H NMR (500 MHz, CDCL3) δ(ppm): 5.18 (2H, s), 6.55 (2H, d, J=7.8 Hz), 7.14 (2H, d, J=9.0 Hz), 7.36-7.47 (5H, m), 7.50 (2H, d, J=8.6 Hz), 7.68 (2H, d, J=7.8 Hz), 8.17 (2H, d, J=8.8 Hz), 8.33 (2H, d, J=8.6 Hz). 13C NMR (125 MHz, CDCL3) δ(ppm): 70.5 (CH2), 115.7 (CH), 116.9, 119.5 (CH), 123.1 (CH), 127.6, 127.7 (CH), 128.6 (CH), 129.0 (CH), 129.7 (CH), 130.4 (CH), 136.1, 138.8 (CH), 145.1, 162.7, 167.7, 176.2, 179.3. MS (FAB+): 422 (MH+). HRMS for C26H19N3O3 (MH+): calculated: 422.1505; found 422.1494.

Workup

  1. temperatureThe solution was refluxed for 21 hours
  2. customthe solvent was removed under reduced pressure
  3. customThe solid residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d53babef0fd44d8191ada59809703531
Source dataset
uspto-grants-2015_06
Patent number
US09045442B2

Reaction notes

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