1,2-Dichloroethane → HCID 178494467, compound

HRID 1631038Notes

Reaction equation

HRID 1631038 reaction equation
[Cl:1][C:2]1[C:3]([OH:12])=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7](=[N:9][OH:10])[NH2:8].Br[C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=O)=[CH:16][C:15]=1[CH2:24]OC.[CH2:27](Cl)[CH2:28]Cl>CC#N.N1C=CC=CC=1>[Cl:1][C:2]1[C:3]([OH:12])=[N:4][CH:5]=[C:6]([C:7]2[N:8]=[C:24]([C:15]3[CH:14]=[CH:23][C:22]([C:5]4[CH:6]=[CH:11][CH:2]=[CH:3][C:27]=4[CH3:28])=[C:17]([CH2:18][O:20][CH3:21])[CH:16]=3)[O:10][N:9]=2)[CH:11]=1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 58554220Methyl 4-bromo-3-(methoxymethyl)benzoateHCID 178513390HCID 178513390, compound

Product 1

HCID 178494467HCID 178494467, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-chloro-N′,6-dihydroxynicotinimidamide (Bionet, 1.46 g; 7.78 mmol) and Intermediate A1 (1.66 g; 6.48 mmol) in MeCN (50 mL) was added EDC (1.61 g; 8.42 mmol). The reaction mixture was stirred at ambient temperature for 18 h. The reaction mixture was diluted with pyridine (20 mL) and heated at 115° C. for 24 hours. The solvent was removed in vacuo and the residue dissolved in DCM. The mixture was washed with water and the organic phase passed through a hydrophobic frit. The solvent was evaporated in vacuo. The residue was purified by flash chromatography on silica, eluting with iso-hexane/EtOAc (100% iso-hexane to 100% EtOAc) to afford the title product as an off-white solid. 1H NMR (DMSO-d6, 400 MHz) δ 12.84 (1 H, s), 8.32 (1 H, s), 8.26 (1 H, d, J=2.3 Hz), 8.21 (1 H, d, J=2.4 Hz), 8.17 (1 H, dd, J=7.9, 1.9 Hz), 7.45 (1 H, d, J=7.9 Hz), 7.41-7.37 (2 H, m), 7.34-7.29 (1 H, m), 7.17 (1 H, d, J=7.4 Hz), 4.22 (2 H, q, J=9.4 Hz), 3.27 (3 H, s), 2.06 (3 H, s). LC/MS: 408 (M+H)+. HPLC (Method C) Rt 3.79 min (Purity: 99.4%).

Workup

  1. temperatureheated at 115° C. for 24 hours
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue dissolved in DCM
  4. washThe mixture was washed with water
  5. customThe solvent was evaporated in vacuo
  6. customThe residue was purified by flash chromatography on silica
  7. washeluting with iso-hexane/EtOAc (100% iso-hexane to 100% EtOAc)

Sources & evidence

ORD record
ord-0eed7a2d280e4ad0bfe643b21a4ae876
Source dataset
uspto-grants-2014_07
Patent number
US08791142B2

Reaction notes

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