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1,1-Dichloroethane → 2-({4-[6-(4-hydroxy-3-methylphenyl)-2-oxo-2,3-dihydropyrimidin-4-yl]phenyl}oxy)-N-(2-piperidin-1-ylethyl)acetamide

HRID 884659
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HRID 884659 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:15]3[CH:20]=CC(OCC(O)=O)=[CH:17][CH:16]=3)[NH:11][C:12](=[O:14])[N:13]=2)=[CH:4][C:3]=1[CH3:26].[O:27]1[CH2:32][CH2:31][N:30]([CH2:33][CH2:34][NH2:35])[CH2:29][CH2:28]1.[OH:36]N1C2C=CC=CC=2N=N1.CCN=C=N[CH2:51][CH2:52][CH2:53][N+](C)(C)C.[I-].Cl[CH:60](Cl)[CH3:61]>CN(C)C=O>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:15]3[CH:16]=[CH:17][C:32]([O:27][CH2:28][C:29]([NH:30][CH2:33][CH2:34][N:35]4[CH2:51][CH2:52][CH2:53][CH2:61][CH2:60]4)=[O:36])=[CH:31][CH:20]=3)[NH:11][C:12](=[O:14])[N:13]=2)=[CH:4][C:3]=1[CH3:26]
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참가 물질

7

반응물 5

HCID 63651,1-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 1222421-(3-(Dimethylamino)propyl)-3-ethylcarbodiimide methiodideHCID 4082852-MorpholinoethylamineHCID 136052111({4-[6-(4-Hydroxy-3-methylphenyl)-2-oxo-2,3-dihydropyrimidin-4-yl]phenyl}oxy)acetic acid2회

생성물 1

HCID 136052070
2-({4-[6-(4-hydroxy-3-methylphenyl)-2-oxo-2,3-dihydropyrimidin-4-yl]phenyl}oxy)-N-(2-piperidin-1-ylethyl)acetamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

({4-[6-(4-hydroxy-3-methylphenyl)-2-oxo-2,3-dihydropyrimidin-4-yl]phenyl}oxy)-acetic acid (Compound 266, 17 mg, 48 umol) and 2-morpholinoethanamine (5.2 mg, 40 umol) were dissolved in dichloroethane (1.25 mL) and N,N-dimethylformamide (0.79 mL). To this solution was added 1-hydroxybenzotriazole (6.8 mg, 50 umol) followed by 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide methiodide (17.8 mg, 60 umol). The reaction mixture was stirred at room temperature for 15 hours and was concentrated in vacuo. The reaction mixture was purified by reverse phase HPLC to give 5 mg of product. 1H NMR (400 MHz, d6-DMSO): δ 8.23 (s, 1H), 8.14 (d, 2H), 8.03 (t, 1H), 7.94 (s, 1H), 7.85 (d, 1H), 7.33 (s, 1H), 7.09 (dd, 2H), 6.90 (d, 1H), 4.59 (s, 2H), 3.27-3.24 (m, 2H), 2.37-2.33 (m, 6H), 2.20 (s, 3H), 1.49-1.44 (m, 4H), 1.38-1.34 (m, 2H). MS (EI): 464 (MH+).

후처리

  1. concentrationwas concentrated in vacuo
  2. customThe reaction mixture was purified by reverse phase HPLC

출처 및 근거

ORD 기록
ord-366d905effc44422a234943e3b80a819
출처 데이터셋
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08242129B2

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