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Benzylamine → N-benzyl-2-(3-(6-(4-hydroxy-3-methylphenyl)-2-oxo-2,3-dihydropyrimidin-4-yl)phenoxy)acetamide

HRID 422064
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HRID 422064 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:15]3[CH:16]=[C:17]([O:21][CH2:22][C:23]([OH:25])=O)[CH:18]=[CH:19][CH:20]=3)[NH:11][C:12](=[O:14])[N:13]=2)=[CH:4][C:3]=1[CH3:26].[CH2:27]([NH2:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.ON1C2C=CC=CC=2N=N1.CCN=C=NCCC[N+](C)(C)C.[I-]>ClC(Cl)C.CN(C)C=O>[CH2:27]([NH:34][C:23](=[O:25])[CH2:22][O:21][C:17]1[CH:18]=[CH:19][CH:20]=[C:15]([C:10]2[NH:11][C:12](=[O:14])[N:13]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([OH:1])=[C:3]([CH3:26])[CH:4]=3)[CH:9]=2)[CH:16]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 7504BenzylamineHCID 757711-HydroxybenzotriazoleHCID 1222421-(3-(Dimethylamino)propyl)-3-ethylcarbodiimide methiodideHCID 178422597({3-[6-(4-Hydroxy-3-methylphenyl)-2-oxo-2,3-dihydropyrimidin-4-yl]phenyl}oxy)acetic acid

생성물 1

HCID 178422595N-benzyl-2-(3-(6-(4-hydroxy-3-methylphenyl)-2-oxo-2,3-dihydropyrimidin-4-yl)phenoxy)acetamide수율 25.5%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 63651,1-Dichloroethane용매

실험 절차

To a solution of ({3-[6-(4-hydroxy-3-methylphenyl)-2-oxo-2,3-dihydropyrimidin-4-yl]phenyl}oxy)acetic acid (16.9 mg, 48 μmol) and benzylamine (4.3 mg, 40 umol) in dichloroethane (1.25 mL) and N,N-dimethylformamide (0.79 mL) was added 1-hydroxybenzotriazole (6.8 mg, 50 μmol) followed by 1-[3-(Dimethylamino)propyl]-3-ethylcarbodiimide methiodide (17.8 mg, 60 μmol). The resultant mixture was stirred at room temperature for 15 hours. The reaction mixture was concentrated in vacuo. Purification of the residue by HPLC (reverse-phase, acetonitrile/water with 0.1% formic acid) followed by concentration in vacuo gave the title compound N-benzyl-2-(3-(6-(4-hydroxy-3-methylphenyl)-2-oxo-2,3-dihydropyrimidin-4-yl)phenoxy)acetamide (4.5 mg, 25%).

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customPurification of the residue by HPLC (reverse-phase, acetonitrile/water with 0.1% formic acid)
  3. concentrationfollowed by concentration in vacuo

출처 및 근거

ORD 기록
ord-c30aecb67c574d0bb9e77e3876c3d991
출처 데이터셋
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08101625B2

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