1,2-Dichloroethane → HCID 67135958, compound

HRID 1631035Notes

Reaction equation

HRID 1631035 reaction equation
[OH:1][N:2]=[C:3]([C:5]1[CH:6]=[CH:7][C:8]([CH2:11][N:12]([CH3:21])[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[N:9][CH:10]=1)[NH2:4].Br[C:23]1[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=O)=[CH:25][C:24]=1[CH2:33]OC.[CH2:36](Cl)[CH2:37]Cl>CC#N.N1C=CC=CC=1>[CH3:30][O:29][CH2:27][C:26]1[CH:25]=[C:24]([C:33]2[O:1][N:2]=[C:3]([C:5]3[CH:6]=[CH:7][C:8]([CH2:11][N:12]([CH3:21])[CH2:13][C:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15])=[N:9][CH:10]=3)[N:4]=2)[CH:23]=[CH:32][C:31]=1[C:8]1[CH:7]=[CH:6][CH:5]=[CH:3][C:36]=1[CH3:37]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 58554220Methyl 4-bromo-3-(methoxymethyl)benzoateHCID 86660281HCID 86660281, compound

Product 1

HCID 67135958HCID 67135958, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of tert-butyl 2-(((5-(N′-hydroxycarbamimidoyl)pyridin-2-yl)methyl)(methyl)amino)acetate (0.750 g; 2.55 mmol) and Intermediate A1 (0.654 mg; 2.55 mmol) in MeCN (9 mL) was added EDC (0.538 g; 2.81 mmol). The reaction mixture was stirred at ambient temperature for 18 h. The reaction mixture was diluted with pyridine (9 mL) and heated at 150° C. in the microwave for 30 minutes. 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 (1:1), affording the title product. 1H NMR (CDCl3, 400 MHz) δ 9.35-9.34 (1 H, m), 8.46-8.43 (2 H, m), 8.19-8.17 (1 H, m), 7.71-7.68 (1 H, m), 7.36-7.28 (4 H, m), 7.14-7.12 (1 H, m), 4.27-4.20 (2 H, m), 3.95 (2 H, s), 3.33 (3 H, s), 3.21 (2 H, s), 2.46 (3 H, s), 2.05 (3 H, s), 1.50 (9 H, s).

Workup

  1. temperatureheated at 150° C. in the microwave for 30 minutes
  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 (1:1)

Sources & evidence

ORD record
ord-458d143041fe4142975214ee9d7de7f3
Source dataset
uspto-grants-2014_07
Patent number
US08791142B2

Reaction notes

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