Ethyl Acetate → {2-[3-(4-Bromo-2-dimethylcarbamoyl-phenyl)-ureido]-ethyl}-methyl-carbamic acid tert-butyl ester

HRID 2234675Notes

Reaction equation

[C:1]([O:5][C:6](=[O:12])[N:7]([CH2:9][CH2:10][NH2:11])[CH3:8])([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.[Br:22][C:23]1[CH:24]=[CH:25][C:26]([N:34]=[C:35]=[O:36])=[C:27]([CH:33]=1)[C:28]([N:30]([CH3:32])[CH3:31])=[O:29].C(OCC)(=O)C>CN(C=O)C>[C:1]([O:5][C:6](=[O:12])[N:7]([CH2:9][CH2:10][NH:11][C:35]([NH:34][C:26]1[CH:25]=[CH:24][C:23]([Br:22])=[CH:33][C:27]=1[C:28](=[O:29])[N:30]([CH3:31])[CH3:32])=[O:36])[CH3:8])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of (2-amino-ethyl)-methyl-carbamic acid tert-butyl ester (100 mg, 0.574 mmol) in DMF (2 mL) was added diisopropylethylamine (0.3 mL, 1.75 mmol) and 5-bromo-2-isocyanato-N,N-dimethyl-benzamide (154 mg, 0.572 mmol). The solution was stirred for 18 hours at 80° C. Ethyl acetate was added to the reaction mixture, and the combined mixture was washed 3 times with water. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The crude material was recrystallized from a mixture of ethyl acetate and dichloromethane to give 75 mg (30%) of {2-[3-(4-bromo-2-dimethylcarbamoyl-phenyl)-ureido]-ethyl}-methyl-carbamic acid tert-butyl ester. 1H-NMR (250 MHz, CDCl3) δ 11.0 (br s, 1H), 8.35 (d, J=9.1 mmol), 7.77 (s, 1H), 7.57 (s, 1H), 7.42 (d, J=9.0 Hz, 1H), 3.45-3.55 (m, 5H), 2.97 (s, 6H), 2.86 (s, 3H), 1.12 (s, 9H).

Workup

washthe combined mixture was washed 3 times with water
dry with materialThe organic layer was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude material was recrystallized from a mixture of ethyl acetate and dichloromethane

Sources & evidence

ORD record: ord-5a5f770a6c9f42a7a078a49d283b8abc
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709645B2

Reaction notes

Loading…