Pyridine → HCID 50910548, compound

HRID 1484541Notes

Reaction equation

HRID 1484541 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:17])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[Br:16])[CH:5]=[CH:6][CH:7]=1.ClCCl.N1C=CC=CC=1.[C:27](Cl)(=[O:32])[CH2:28][CH:29]([CH3:31])[CH3:30]>C(OCC)(=O)C>[Br:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:9]([NH:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][C:27](=[O:32])[CH2:28][CH:29]([CH3:31])[CH3:30])[CH:3]=1)=[O:17]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 66054Isovaleryl chlorideHCID 784673N-(3-Aminophenyl)-2-bromobenzene-1-carboximidic acid

Product 1

HCID 50910548HCID 50910548, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

N-(3-Aminophenyl)-2-bromobenzamide (50 mg, 0.17 mmol), dichloromethane (1.7 mL), pyridine (17 μL, 0.21 mmol), and isovaleryl chloride (25 μL, 0.21 mmol) were added to a vial with stir bar and stirred for 20 h. The reaction was then diluted with ethyl acetate, then the combined organics were washed with 1 M aqueous HCl, then half-saturated aqueous NaHCO3, then brine. The crude solution was dried over Na2SO4, filtered, and concentrated to a colorless oil, then purified by column chromatography (EtOAc/hexanes gradient) after dry-loading on SiO2. The title compound was obtained as a white solid (53 mg, 82%). LRMS (ESI+) (M+H): 375.05.

Workup

  1. stirringstirred for 20 h
  2. washthe combined organics were washed with 1 M aqueous HCl
  3. dry with materialThe crude solution was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to a colorless oil
  6. custompurified by column chromatography (EtOAc/hexanes gradient)
  7. customafter dry-loading on SiO2

Sources & evidence

ORD record
ord-3ffa7d00eba944d2a081b7017d65a48c
Source dataset
uspto-grants-2016_08
Patent number
US09422262B2

Reaction notes

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