Hydrochloric Acid → (E)-N-(6-(2-aminophenylamino)-6-oxohex-4-enyl)benzamide

HRID 1776147Notes

Reaction equation

HRID 1776147 reaction equation
[C:1]([NH:9][CH2:10][CH2:11][CH2:12]/[CH:13]=[CH: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])/[CH:14]=[CH:13]/[CH2:12][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 67283444(E)-tert-butyl 2-(6-benzamidohex-2-enamido)phenylcarbamate

Product 1

HCID 45138789(E)-N-(6-(2-aminophenylamino)-6-oxohex-4-enyl)benzamideYield 62%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of (E)-tert-butyl 2-(6-benzamidohex-2-enamido)phenylcarbamate (14)(170 mg, 0.402 mmol) in propan-2-ol (10 mL). The mixture was stirred at 0° C. with HCl gas for 1 hour, 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-4-enyl)benzamide (71.6 mg, yield 62%) as an off-white solid after purification by column chromatography (eluent: DCM:MeOH=50:1). 1H NMR (300 MHz, DMSO): δ 1.724 (t, 2H), 2.258 (t, 2H), 3.465 (m, 2H), 4.875 (s, 1H), 6.165-6.216 (d, J=15.3 1H), 6.511-6.991 (m, 4H), 7.232-7.258 (d, 1H), 7.425-7.512 (m, 3H). 7.802-7.852 (m, 2H), 8.507 (s, 1H), 9.200 (s, 1H); LC-MS found 324 (M+H)+; HPLC (214 nm, 99.6%, 254 nm, 100%).

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-872db67ab4fa4c20aa91965adfa574ec
Source dataset
uspto-grants-2016_02
Patent number
US09265734B2

Reaction notes

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