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1-Hydroxybenzotriazole → (E)-N-[3-(4-chlorophenyl)-2-oxo-tetrahydropyrimidin-1-yl]-3-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]acrylamide

HRID 546751
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HRID 546751 반응식
C(N(C(C)C)CC)(C)C.[NH2:10][N:11]1[CH2:16][CH2:15][CH2:14][N:13]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[C:12]1=[O:24].C1C=CC2N(O)N=NC=2C=1.[CH3:35][O:36][C:37]1[N:42]=[C:41](/[CH:43]=[CH:44]/[C:45](O)=[O:46])[CH:40]=[CH:39][C:38]=1[N:48]1[CH:52]=[C:51]([CH3:53])[N:50]=[CH:49]1>CN(C=O)C.C(OCC)(=O)C.C(Cl)CCl>[Cl:23][C:20]1[CH:19]=[CH:18][C:17]([N:13]2[CH2:14][CH2:15][CH2:16][N:11]([NH:10][C:45](=[O:46])/[CH:44]=[CH:43]/[C:41]3[CH:40]=[CH:39][C:38]([N:48]4[CH:52]=[C:51]([CH3:53])[N:50]=[CH:49]4)=[C:37]([O:36][CH3:35])[N:42]=3)[C:12]2=[O:24])=[CH:22][CH:21]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 66633906(E)-3-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]acrylic acidHCID 668394801-Amino-3-(4-chlorophenyl)tetrahydropyrimidin-2-one

생성물 1

HCID 66839690(E)-N-[3-(4-chlorophenyl)-2-oxo-tetrahydropyrimidin-1-yl]-3-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]acrylamide
수율 99.8%

시약·촉매·용매 3

HCID 111,2-Dichloroethane용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

IPEA (0.65 mL), 1-amino-3-(4-chlorophenyl)tetrahydropyrimidin-2-one (139 mg), EDC (177 mg) and HOBT (125 mg) were added to a solution of (E)-3-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]acrylic acid (300 mg) in DMF (6 mL) at room temperature. The reaction solution was stirred at room temperature for 24 hours. The reaction solution was diluted with ethyl acetate and washed with a saturated sodium bicarbonate solution and a saturated sodium chloride solution. The resulting organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: heptane-ethyl acetate system, then ethyl acetate-methanol system) to obtain 287 mg of the title compound. The property value of the compound is as follows.

후처리

  1. washwashed with a saturated sodium bicarbonate solution
  2. dry with materialThe resulting organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (carrier
  5. washelution solvent

출처 및 근거

ORD 기록
ord-722965baade74aa09ac7245d3f8994ac
출처 데이터셋
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07935815B2

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