[1-(3-Chloro-4-cyano-2-methylphenyl)-3-methyl-2,5-dioxoimidazolidin-4-ylmethyl]carbamic Acid tert-butyl Ester → HCID 69516096, compound

HRID 853823Notes

Reaction equation

HRID 853823 reaction equation
C(OC(=O)[NH:7][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>[NH2:7][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]

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 69516096HCID 69516096, compoundYield 180.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of the N-Boc-protected amine 13B (260 mg, 0.662 mmol) in CH2Cl2 (3 mL) and TFA (3 mL) was stirred at rt for 1.5 h. The solution was then concentrated under reduced pressure to afford the title compound (349 mg) as a brown foam as the TFA salt. 1H NMR (CD3OD) δ 2.32, 2.33 (s, 3H), 3.07, 3.09 (s, 3H), 3.49-3.64 (m, 2H), 4.50-4.52 (m, 1H), 4.63-4.65 (m, 1H), 7.46 (d, J=8.3 Hz, 1H), 7.79, 7.80 (d, J=8.23 Hz, 1H); HPLC a) column: Phenominex 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, 1.50, 1.65 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, 0.90, 1.11 min retention time (90%); MS (ES) m/z 293 [M+H]+.

Workup

  1. concentrationThe solution was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-f173ae9e36d749a98848fb50c8f66ac1
Source dataset
uspto-grants-2007_08
Patent number
US07256208B2

Reaction notes

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