Pyridine → propan-2-yl 3-[(4E)-7-methoxy-4-methoxyimino-2,2-dimethyl-1,3-dihydronaphthalen-1-yl]imidazole-4-carboxylate

HRID 2089528노트

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HRID 2089528 반응식
[CH:1]([O:4][C:5]([C:7]1[N:8]([CH:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH3:23])[CH:20]=3)[C:15](=O)[CH2:14][C:13]2([CH3:26])[CH3:25])[CH:9]=[N:10][CH:11]=1)=[O:6])([CH3:3])[CH3:2].Cl.[CH3:28][O:29][NH2:30].N1C=CC=CC=1>C(O)(C)C.C(OCC)(=O)C>[CH:1]([O:4][C:5]([C:7]1[N:8]([CH:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH3:23])[CH:20]=3)/[C:15](=[N:30]/[O:29][CH3:28])/[CH2:14][C:13]2([CH3:25])[CH3:26])[CH:9]=[N:10][CH:11]=1)=[O:6])([CH3:2])[CH3:3]

참가 물질

6

반응물 3

HCID 1049PyridineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 591993943-(7-methoxy-2,2-dimethyl-4-oxo-1,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid isopropyl ester

생성물 1

HCID 59199326propan-2-yl 3-[(4E)-7-methoxy-4-methoxyimino-2,2-dimethyl-1,3-dihydronaphthalen-1-yl]imidazole-4-carboxylate

시약·촉매·용매 2

HCID 3776Isopropanol용매HCID 8857Ethyl Acetate용매

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온도
50 °C

실험 절차

To a solution of 3-(7-methoxy-2,2-dimethyl-4-oxo-1,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid isopropyl ester, which can be prepared as described in Example 14, (0.053 g, 0.147 mmol) and methoxyamine hydrochloride (0.038 g, 0.442 mmol) in isopropanol (1 mL) is added pyridine (0.118 g, 1.472 mmol). The mixture is heated to 50° C. and after 2 hours, is diluted with ethyl acetate, and washed twice with 1M aqueous sodium bisulfate, water, and brine. The organic phase is dried over MgSO4, filtered and concentrated. The resulting residue is purified by silica gel flash chromatography (elution with heptane-ethyl acetate, 4:1 to 7:3) to give 3-{7-methoxy-4-[(E)-methoxyimino]-2,2-dimethyl-1,2,3,4-tetrahydro-naphthalen-1-yl}-3H-imidazole-4-carboxylic acid isopropyl ester; MS: (ESI) m/z 386.0 (M+H)+. The HCl salt of the title compound can be prepared by dissolution in diethyl ether followed by treatment with an excess of 1N HCl in diethyl ether. The resulting heterogeneous solution is concentrated to furnish the HCl salt of 3-{7-Methoxy-4-[(E)-methoxyimino]-2,2-dimethyl-1,2,3,4-tetrahydro-naphthalen-1-yl}-3H-imidazole-4-carboxylic acid isopropyl ester; 1H NMR (400 MHz, MeOD) δ ppm 0.96 (s, 3 H), 1.12 (s, 3 H), 1.47 (d, J=6.1 Hz, 3 H), 1.49 (d, J=6.3 Hz, 3 H), 2.43 (d, J=17.9 Hz, 1 H), 3.01 (d, J=17.9 Hz, 1 H), 3.82 (s, 3 H), 4.04 (s, 3 H), 5.40 (sept, J=6.3 Hz, 1 H), 6.65 (s, 1 H), 6.79 (d, J=2.5 Hz, 1 H), 7.09 (dd, J=9.1, 2.5 Hz, 1 H), 8.16 (d, J=9.1 Hz, 1 H), 8.30 (s, 1 H), 8.53 (s, 1 H).

후처리

  1. washwashed twice with 1M aqueous sodium bisulfate, water, and brine
  2. dry with materialThe organic phase is dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting residue is purified by silica gel flash chromatography (elution with heptane-ethyl acetate, 4:1 to 7:3)

출처 및 근거

ORD 기록
ord-6eec109239144dedb8fbe82f0473e5a5
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08436035B2

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