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Ethyl isocyanate → 4-Amino-2-(3-ethylureido)-N-(1-hydroxy-1,3-dihydrobenzo[c][1, 2]oxaborol-6-yl)benzenesulfonamide

HRID 1256178
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HRID 1256178 반응식
[NH2:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[CH:14]=[CH:15][C:16]2[CH2:20][O:19][B:18]([OH:21])[C:17]=2[CH:22]=1)(=[O:11])=[O:10].[N:23]([CH2:26][CH3:27])=[C:24]=[O:25]>CN(C=O)C.C(OCC)(=O)C>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([S:9]([NH:12][C:13]2[CH:14]=[CH:15][C:16]3[CH2:20][O:19][B:18]([OH:21])[C:17]=3[CH:22]=2)(=[O:10])=[O:11])=[C:2]([NH:1][C:24]([NH:23][CH2:26][CH3:27])=[O:25])[CH:7]=1
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참가 물질

5

반응물 2

HCID 8022Ethyl isocyanateHCID 671737422,4-diamino-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)benzenesulfonamide

생성물 1

HCID 673124054-Amino-2-(3-ethylureido)-N-(1-hydroxy-1,3-dihydrobenzo[c][1, 2]oxaborol-6-yl)benzenesulfonamide수율 24.6%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate
용매

실험 절차

To a solution of 2,4-diamino-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)benzenesulfonamide (1.0 g, 3.13 mmol) in DMF (15 ml) was added isocyanatoethane (0.5 g, 7.0 mmol) dropwise at room temperature. The reaction mixture was stirred at room temperature overnight, diluted with ethyl acetate and washed with H2O, brine. The organic fraction was then dried (MgSO4) and concentrated in vacuo. The residue was purified by Prep-HPLC to give the title compound as a white powder (0.3 g). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.87 (s, 1H), 9.17 (s, 1H), 7.99 (s, 1H), 7.43 (d, J=1.6 Hz, 1H), 7.34 (d, J=2.0 Hz, 1H), 7.31 (d, J=8.4 Hz, 1H), 7.24 (d, J=8.0 Hz, 1H), 7.12 (dd, J=2.0, 8.4 Hz, 1H), 7.02 (t, J=5.2 Hz, 1H), 6.08 (dd, J=2.0, 8.4 Hz, 1H), 5.88 (s, 2H), 4.87 (s, 2H), 3.04˜3.11 (m, 2H), 1.07 (t, J=7.2 Hz, 3H); MS (ESI) m/z=389 (M−1, negative); HPLC purity: 93.6% (MaxPlot 200-400 nm), 90.3% (220 nm).

후처리

  1. washwashed with H2O, brine
  2. dry with materialThe organic fraction was then dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by Prep-HPLC

출처 및 근거

ORD 기록
ord-2d30f9293bc54d8c9f56c0963618fa40
출처 데이터셋
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08461134B2

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