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

HRID 1013460

반응식

HRID 1013460 반응식
[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]

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 46406714-Bromomethyl benzoyl bromideHCID 57717474tert-Butyl (2-amino-4-(thiophen-2-yl)phenyl)carbamate

생성물 1

HCID 57925962Tert-butyl [2-{[4-(bromomethyl)benzoyl]amino}-4-(2-thienyl)phenyl]carbamate

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 6344Dichloromethane용매

반응 조건

온도
-78 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-f5ea022b28b947cca98a473ee054d7a3
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981874B2

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