Hydrochloric Acid → (E)-N-(6-(2-aminophenylamino)-6-oxohex-3-enyl)benzamide

HRID 1776148Notes

Reaction equation

HRID 1776148 reaction equation
[C:1]([NH:9][CH2:10][CH2:11]/[CH:12]=[CH:13]/[CH2:14][C:15]([NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[NH:24]C(=O)OC(C)(C)C)=[O:16])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C([O-])([O-])=O.[K+].[K+]>CC(O)C>[NH2:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[NH:17][C:15](=[O:16])[CH2:14]/[CH:13]=[CH:12]/[CH2:11][CH2:10][NH:9][C:1](=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 60207724(E)-tert-butyl 2-(6-benzamidohex-3-enamido)phenylcarbamate

Product 1

HCID 45138499(E)-N-(6-(2-aminophenylamino)-6-oxohex-3-enyl)benzamideYield 20.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of (E)-tert-butyl 2-(6-benzamidohex-3-enamido)phenylcarbamate (15)(130 mg, 0.307 mmol) in propan-2-ol (10 mL) was bubbled HCl gas for 1 hour at 0° C. To the reaction mixture was added 10% K2CO3 to adjust the pH value to 7-8, then the mixture was extracted with DCM (3×50 mL), the combined organic layers were washed with brine, dried over Na2SO4 and concentrated to give the desired compound of (E)-N-(6-(2-aminophenylamino)-6-oxohex-3-enyl)benzamide (16) (20 mg, 20%) as an off-white solid after purification by column chromatography (eluent: DCM:MeOH=50:1). 1H NMR (300 MHz, DMSO): δ 2.418 (m, 2H), 3.257 (m, 2H), 4.847 (s, 2H), 5.572-5.716 (m, 2H), 6.519-6.570 (m, 1H), 67.424-7.549 (m, 3H), 7.833-7.861 (t, 2H). 8.532-8.576 (t, 2H), 9.149 (s, 1H); LC-MS found 324 (M+H)+; HPLC (214 nm, 98%, 254 nm, 98%).

Workup

  1. extractionthe mixture was extracted with DCM (3×50 mL)
  2. washthe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4e8afa4f35cf47ffb17452bc63c95a79
Source dataset
uspto-grants-2016_02
Patent number
US09265734B2

Reaction notes

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