Acetic Acid → HCID 58467922, compound

HRID 1614937Notes

Reaction equation

HRID 1614937 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:11]=[C:12]([NH:16][C:17](=[O:27])[C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-])=O)[CH:19]=3)[CH:13]=[CH:14][CH:15]=2)[C:5]([Cl:28])=[CH:4][N:3]=1.CO.C(O)(=O)C.C([O-])(O)=O.[Na+]>[Fe].CCOC(C)=O.O>[NH2:24][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=1)[C:17]([NH:16][C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([CH2:9][NH:8][C:6]2[C:5]([Cl:28])=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=2)[CH:11]=1)=[O:27]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 516892Sodium BicarbonateHCID 86643682HCID 86643682, compound

Product 1

HCID 58467922HCID 58467922, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

Into a reaction flask were added N-(3-{[(2,5-dichloropyrimidin-4-yl)amino]methyl}phenyl)-3-nitrobenzamide (0.30 g, 0.72 mmol), methanol (20 mL), acetic acid (2.0 mL), and water (1 mL). Then iron (0.50 g, 9.0 mmol) powder was added. The reaction mixture was heated at 70° C. overnight. After cooling, the mixture was filtered and washed with EtOAc. The filtrate was concentrated under vacuum to give a residue, which was treated with NaHCO3 (saturated aqueous solution) and EtOAc. The organic layer was dried and concentrated under vacuum to provide the desired product (0.27 g, 97%). LCMS for C18H16Cl2N5O (M+H)+: m/z=388.0, 390.0.

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered
  3. washwashed with EtOAc
  4. concentrationThe filtrate was concentrated under vacuum
  5. customto give a residue, which
  6. customThe organic layer was dried
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-dddabab66c674693ae9e807fc14cc11f
Source dataset
uspto-grants-2014_07
Patent number
US08765727B2

Reaction notes

Loading…