Water → N-hydroxy-4-[2-(benzofuran-2-yl-carbonylamino)-ethoxy]-benzamide

HRID 29699

반응식

HRID 29699 반응식
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([OH:12])=O.CCN=C=NCCCN(C)C.Cl.C1C=CC2[N:33]([OH:34])N=NC=2C=1.O.Cl.[NH2:37][CH2:38][CH2:39][O:40][C:41]1[CH:50]=[CH:49][C:44]([C:45](OC)=[O:46])=[CH:43][CH:42]=1.C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C>[OH:34][NH:33][C:45](=[O:46])[C:44]1[CH:49]=[CH:50][C:41]([O:40][CH2:39][CH2:38][NH:37][C:10]([C:2]2[O:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[CH:3]=2)=[O:12])=[CH:42][CH:43]=1

참가 물질

9

반응물 6

HCID 962WaterHCID 8471TriethylamineHCID 10331Benzofuran-2-carboxylic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 50988568Methyl 4-(2-aminoethoxy)benzoate hydrochloride

생성물 1

HCID 24971310N-hydroxy-4-[2-(benzofuran-2-yl-carbonylamino)-ethoxy]-benzamide

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of benzofuran-2-carboxylic acid (0.162 g, 1 mmol), EDC.HCl (0.268 g, 1.4 mmol) and HOBT.H2O (0.203 g, 1.5 mmol) in DMF (6 ml) was stirred for 2 h. Methyl 4-(2-aminoethoxy)benzoate hydrochloride (0.232 g, 1 mmol) was added followed by triethylamine (0.121 g, 1.2 mmol). The reaction mixture was stirred for 2 h and then diluted with ethyl acetate, washed with saturated sodium bicarbonate solution, and brine. The organic layer was concentrated in vacuo and the crude 4-[2-(benzofuran-2-ylcarbonylamino)ethoxy]-benzoate was converted to the title compound as described in Example 1, Step 5 above. 1H NMR (DMSO-d6) δ 11.05 (s, 1H), 8.92 (t, J=5.6 Hz, 1H), 8.88 (s, 1H), 7.76 (d, J=8.0 Hz, 1H), 7.70 (d, J=9.2 Hz, 2H), 7.64 (d, J=8.0 Hz, 1H), 7.55 (s, 1H), 7.46 (t, J=6.8 Hz, 1H), 7.32 (t, J=8.0 Hz, 1H), 7.01 (d, J=8.2 Hz, 2H), 4.18 (t, J=5.6 Hz, 2H), 3.67 (m, 2H). EM (calc.): 340.1; MS (ESI) m/e: (M+1H)+: 341.0, (M−1H)−: 339.1.

후처리

  1. washwashed with saturated sodium bicarbonate solution, and brine
  2. concentrationThe organic layer was concentrated in vacuo

출처 및 근거

ORD 기록
ord-711ae2169e79473582a71d6d68995e0c
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07420089B2

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