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

HRID 2089528ノート

反応式

HRID 2089528 の反応式
[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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3776Isopropanol溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-6eec109239144dedb8fbe82f0473e5a5
出典データセット
uspto-grants-2013_05
特許番号
US08436035B2

反応ノート

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