Diisopropylethylamine → Tert-butyl [2-{[4-(bromomethyl)benzoyl]amino}-4-(2-thienyl)phenyl]carbamate

HRID 1013460

Reaction equation

[Br:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](Br)=[O:8])=[CH:5][CH:4]=1.[C:12]([O:16][C:17](=[O:31])[NH:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[S:26][CH:27]=[CH:28][CH:29]=2)=[CH:21][C:20]=1[NH2:30])([CH3:15])([CH3:14])[CH3:13].CCN(C(C)C)C(C)C>C(Cl)Cl.Cl>[C:12]([O:16][C:17](=[O:31])[NH:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[S:26][CH:27]=[CH:28][CH:29]=2)=[CH:21][C:20]=1[NH:30][C:7](=[O:8])[C:6]1[CH:10]=[CH:11][C:3]([CH2:2][Br:1])=[CH:4][CH:5]=1)([CH3:15])([CH3:13])[CH3:14]

Participants

Conditions

Temperature: -78 °C

Procedure

4-Bromomethyl-benzoyl bromide (0.70 g, 2.52 mmol) was made 0.21 M in anhydrous DCM and cooled to −78° C. To this stirring solution was added (2-amino-4-thiophen-2-yl-phenyl)-carbamic acid tert-butyl ester (0.73 g, 2.52 mmol) followed by DIPEA (0.98 g, 7.56 mmol). The resulting solution was warmed to ambient temperature and stirred for 18 hours. The reaction mixture was then diluted with 0.1 N HCl and extracted with EtOAc. The organic layer was then washed with saturated aqueous sodium bicarbonate, brine, dried (MgSO4), and concentrated in vacuo to afford the title compound: 1H NMR (DMSO-d6, 600 MHz) 9.90 (s, 1H), 8.72 (s, 1H), 7.94 (d, J=7.8. Hz, 2H), 7.78-7.80 (m, 1H), 7.57-7.62 (m, 3H), 7.47-7.51 (m, 2H), 7.42-7.44 (m, 1H), 7.09-7.12 (m, 1H), 4.77 (s, 2H), 1.43 (s, 9H).

Workup

temperatureThe resulting solution was warmed to ambient temperature
extractionextracted with EtOAc
washThe organic layer was then washed with saturated aqueous sodium bicarbonate, brine
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-f5ea022b28b947cca98a473ee054d7a3
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981874B2

Linked notes

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