Hydrochloric Acid → HCID 60207706, compound

HRID 1776132Notes

Reaction equation

HRID 1776132 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15](=[O:32])/[CH:16]=[CH:17]/[CH2:18][CH2:19][CH2:20][N:21]1[C:29](=[O:30])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]1=[O:31])(C)(C)C.Cl.C([O-])([O-])=O.[K+].[K+]>CC(O)C>[NH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15](=[O:32])/[CH:16]=[CH:17]/[CH2:18][CH2:19][CH2:20][N:21]1[C:29](=[O:30])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]1=[O:31]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 60207711HCID 60207711, compound

Product 1

HCID 60207706HCID 60207706, compoundYield 38.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of (E)-tert-butyl 2-(6-(1,3-dioxoisoindolin-2-yl)hex-2-enamido)phenylcarbamate (3) (135 mg, 0.3 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-(2-aminophenyl)-6-(1,3-dioxoisoindolin-2-yl)hex-2-enamide (40 mg, yield 37%) as an off-white solid after purification by column chromatography (eluent: DCM:MeOH=50:1). 1H NMR (300 MHz, DMSO): δ 1.759-1.830 (m, 2H), 2.202-2.271 (m, 2H), 3.495-3.646 (m, 2H), 4.783 (s, 2H) 6.143-6.194 (d, J=15.3 1H), 6.519-6.692 (m, 1H) 6.705-6.914 (m, 4H), 7.206-7.229 (d, 1H), 7.813-7.891 (d, 2H), 8.350 (m, 4H), 9.175 (s, 1H); LC-MS found 350 (M+H)+, HPLC (214 nm, 99%, 254 nm, 99%).

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-f20be4d63d754786977ed4b50a6f892f
Source dataset
uspto-grants-2016_02
Patent number
US09265734B2

Reaction notes

Loading…