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 910260노트

반응식

HRID 910260 반응식
[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]

참가 물질

7

반응물 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

생성물 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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-61dab7d56cce4b80a5c900d5a2dc261a
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08022061B2

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