[1-(3-Chloro-4-cyano-2-methylphenyl)-3-methyl-2,5-dioxoimidazolidin-4-ylmethyl]carbamic Acid tert-butyl Ester → HCID 58932646, compound

HRID 853822Notes

Reaction equation

HRID 853822 reaction equation
C(OC(=O)N[CH2:8][CH:9]1[C:13](=[O:14])[N:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[C:17]([Cl:23])[C:16]=2[CH3:24])[C:11](=[O:25])[N:10]1[CH3:26])(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[Cl:23][C:17]1[C:16]([CH3:24])=[C:15]([N:12]2[C:13](=[O:14])[C:9](=[CH2:8])[N:10]([CH3:26])[C:11]2=[O:25])[CH:20]=[CH:19][C:18]=1[C:21]#[N:22]

Participants

4

Reactant 1

HCID 69515564[1-(3-Chloro-4-cyano-2-methylphenyl)-3-methyl-2,5-dioxoimidazolidin-4-ylmethyl]carbamic Acid tert-butyl Ester

Product 1

HCID 58932646HCID 58932646, compoundYield 33.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of the N-Boc-protected amine 13B (300 mg, 0.763 mmol) in CH2Cl2 (3 mL) and TFA (3 mL) was stirred at rt for 1 h. The solution was then concentrated under reduced pressure and the residue azeotroped with a 1:1 solution of CH2Cl2/toluene (3×10 mL) and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, CH2Cl2/CH3OH, 100:0 to 80:20 gradient) to afford the title compound (71 mg) as a white solid. 1H NMR (DMSO-d6) δ 2.21 (s, 3H), 3.12 (s, 3H), 5.16 (d, J=2.2 Hz, 1H), 5.39 (d, J=2.2 Hz, 1H), 7.58 (d, J=8.8 Hz, 1H), 7.98 (d, J=8.3 Hz, 1H); 13C NMR (DMSO-d6) δ 15.70, 26.73, 95.59, 113.18, 115.83, 128.79, 132.09, 136.03, 136.37, 136.54, 136.68, 151.88, 160.56; HPLC a) column: Phenominex C18 4.6×50 mm, 4 min gradient, 10% MeOH/90% H2O/0.1% TFA to 90% MeOH/10% H2O/0.1% TFA, 1 min hold, 4 mL/min, UV detection at 220 nm, 2.70 min retention time; HPLC b) column: Shimadzu Shim-Pack VP-ODS C18 4.6×50 mm, 4 min gradient, 10% MeOH/90% H2O/0.1% TFA to 90% MeOH/10% H2O/0.1% TFA, 1 min hold, 4 mL/min, UV detection at 220 nm, 2.59 min retention time (98%).

Workup

  1. concentrationThe solution was then concentrated under reduced pressure
  2. customthe residue azeotroped with a 1:1 solution of CH2Cl2/toluene (3×10 mL)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash chromatography (silica gel, CH2Cl2/CH3OH, 100:0 to 80:20 gradient)

Sources & evidence

ORD record
ord-5786b90ca71a440398551ae72a54a593
Source dataset
uspto-grants-2007_08
Patent number
US07256208B2

Reaction notes

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