反応式
[CH:1]([C:3]1[NH:7][C:6]([C:8]([OH:10])=O)=[CH:5][C:4]=1[CH3:11])=[O:2].[NH2:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>C(#N)C>[N:15]1([CH2:14][CH2:13][NH:12][C:8]([C:6]2[NH:7][C:3]([CH:1]=[O:2])=[C:4]([CH3:11])[CH:5]=2)=[O:10])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1参加物
反応物 5
生成物 1
試薬・触媒・溶媒 1
実験手順
To a suspension of 5-formyl-4-methyl-1H-pyrrole-2-carboxylic acid (2 g, 13 mmol) in acetonitrile was added 4-(2-aminoethyl)morpholine (1.9 mL, 14 mmol), EDC (2.7 g, 14 mmol), HOBt (1.9 g, 14 mmol) and triethylamine (3.6 mL, 26 mmol) sequentially. The reaction mixture was stirred at room temperature for 12 hours and concentrated at reduced pressure. The residue was dissolved in 300 mL of 1N hydrogen chloride solution. The aqueous layer was washed with 150 mL of ethyl acetate twice and basified with sodium bicarbonate. The product was then extracted with 250 mL of dichloromethane twice, dried over MgSO4, and concentrated to afford 1.8 g (53%) of 5-formyl-4-methyl-1H-pyrrole-2-carboxylic acid (2-morpholin4-yl-ethyl)-amide as a yellowish solid. 1H NMR (300 MHz, DMSO-d6) δ 12.19 (br s, 1H, NH), 9.72 (s, 1H, CHO), 8.29 (br t, J=6.6 Hz, 1H, CONH), 6.65 (d, J=1.7 Hz, 1H), 3.5 (m, 4H), 3.3 (m, 2H, CONHCH2), 2.4 (m, 6H), 2.28 (s, 3H, CH3). MS m/z 265 [M+].
後処理
- concentrationconcentrated at reduced pressure
- dissolutionThe residue was dissolved in 300 mL of 1N hydrogen chloride solution
- washThe aqueous layer was washed with 150 mL of ethyl acetate twice
- extractionThe product was then extracted with 250 mL of dichloromethane twice
- dry with materialdried over MgSO4
- concentrationconcentrated
出典と根拠
- ORDレコード
- ord-cb6d25fbe615416297e494dbc68c42c3
- 出典データセット
- uspto-grants-2003_08
- 特許番号
- US06610688B2
関連ノート
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