1,2-Dichloroethane → N-((5-Butyl-1-(5-methyl-4-(thiophen-2-yl)pyrimidin-2-yl)-1H-pyrazol-4-yl)methyl)-2-(1H-imidazol-5-yl)acetamide

HRID 910260ノート

反応式

HRID 910260 の反応式
[CH2:1]([C:5]1[N:9]([C:10]2[N:15]=[C:14]([C:16]3[S:17][CH:18]=[CH:19][CH:20]=3)[C:13]([CH3:21])=[CH:12][N:11]=2)[N:8]=[CH:7][C:6]=1[CH2:22][NH2:23])[CH2:2][CH2:3][CH3:4].[NH:24]1[C:28]([CH2:29][C:30](O)=[O:31])=[CH:27][N:26]=[CH:25]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>C(Cl)Cl>[CH2:1]([C:5]1[N:9]([C:10]2[N:15]=[C:14]([C:16]3[S:17][CH:18]=[CH:19][CH:20]=3)[C:13]([CH3:21])=[CH:12][N:11]=2)[N:8]=[CH:7][C:6]=1[CH2:22][NH:23][C:30](=[O:31])[CH2:29][C:28]1[NH:24][CH:25]=[N:26][CH:27]=1)[CH2:2][CH2:3][CH3:4]

参加物

7

反応物 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 96215Imidazole-4-acetic acidHCID 60207818(5-butyl-1-(5-methyl-4-(thiophen-2-yl)pyrimidin-2-yl)-1H-pyrazol-4-yl)methanamine

生成物 1

HCID 67389980N-((5-Butyl-1-(5-methyl-4-(thiophen-2-yl)pyrimidin-2-yl)-1H-pyrazol-4-yl)methyl)-2-(1H-imidazol-5-yl)acetamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A mixture of (5-butyl-1-(5-methyl-4-(thiophen-2-yl)pyrimidin-2-yl)-1H-pyrazol-4-yl)methanamine and 2-(1H-imidazol-5-yl)acetic acid in 1:1 molar ratio was treated with EDC (1 equiv.), HOBT (1 equiv.) and N-methylmorpholine (2 equiv.) in methylene chloride (at a concentration of 0.5 M) at room temperature overnight (20 hours). Upon completion, an additional methylene chloride was added and the resulting mixture was washed with water and brine, dried over anhydrous sodium sulfate and concentrated. The crude material was purified by column chromatography using 10% CH3OH/CH2Cl2 as the eluent to give the title compound 34. 1H NMR (400 MHz, CD3OD) δ 8.79 (s 1H), 8.34 (t, J=5.48 Hz, 1H), 8.10 (s 1H), 7.94 (s 1H), 7.93 (s 1H), 7.62 (s 1H), 7.33 (D, J=4.69 Hz, 1H), 7.10 (s 1H), 4.18 (D, J=5.48 Hz, 2H), 3.49 (s 3H), 3.11 (t, J=7.83 Hz, 2H), 2.60 (s 3H), 1.40 (quint, J=7.43 Hz, 2H), 1.24 (sex, J=7.83 Hz, 2H), 0.77 (t, J=7.43 Hz, 3H). LCMS (ES+) m/z 436 (M+1).

後処理

  1. washthe resulting mixture was washed with water and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe crude material was purified by column chromatography

出典と根拠

ORDレコード
ord-61dab7d56cce4b80a5c900d5a2dc261a
出典データセット
uspto-grants-2011_09
特許番号
US08022061B2

反応ノート

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