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Dichloromethane → Benzyl 2-(2-(1-(4-(5-(cyclopropylcarbamoyl)-2-methylphenyl)-3-oxo-3,4-dihydropyrazin-2-yl)pyrrolidin-2-yl)phenoxy)ethyl(methyl)carbamate

HRID 2070841
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HRID 2070841 반응식
C(=O)([O-])[O-].[Cs+].[Cs+].[CH:7]1([NH:10][C:11](=[O:38])[C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([N:19]3[CH:24]=[CH:23][NH:22][CH:21]([N:25]4[CH2:29][CH2:28][CH2:27][CH:26]4[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[OH:36])[C:20]3=[O:37])[CH:13]=2)[CH2:9][CH2:8]1.Cl[CH2:40][CH2:41][N:42]([CH3:53])[C:43](=[O:52])[O:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1.C(Cl)Cl>C(#N)C.O>[CH:7]1([NH:10][C:11]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([N:19]3[CH:24]=[CH:23][N:22]=[C:21]([N:25]4[CH2:29][CH2:28][CH2:27][CH:26]4[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[O:36][CH2:40][CH2:41][N:42]([CH3:53])[C:43](=[O:52])[O:44][CH2:45][C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)[C:20]3=[O:37])[CH:13]=2)=[O:38])[CH2:9][CH2:8]1
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참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 13592063Benzyl (2-chloroethyl)methylcarbamateHCID 66689880N-cyclopropyl-3-{3-[2-(2-hydroxyphenyl)pyrrolidin-1-yl]-2-oxo-3,4-dihydropyrazin-1(2H)-yl]-4-methylbenzamide

생성물 1

HCID 66689728Benzyl 2-(2-(1-(4-(5-(cyclopropylcarbamoyl)-2-methylphenyl)-3-oxo-3,4-dihydropyrazin-2-yl)pyrrolidin-2-yl)phenoxy)ethyl(methyl)carbamate
수율 47.2%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

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온도
90 °C

실험 절차

Cesium carbonate (0.274 g) was added to a solution of N-cyclopropyl-3-{3-[2-(2-hydroxyphenyl)pyrrolidin-1-yl]-2-oxo-3,4-dihydropyrazin-1(2H)-yl}-4-methylbenzamide (Example 324a, 0.18 g) and benzyl 2-chloroethyl(methyl)carbamate (0.096 g) in acetonitrile (4 mL), and the reaction was heated at 90° C. for 72 h. DCM and water were added, and the organic layer was separated, dried (Na2SO4) and the solvent removed in is vacuo. Purification (SiO2 chromatography eluting with 30-50% EtOAc in DCM) gave the subtitle compound as an oil (0.122 g).

후처리

  1. customthe organic layer was separated
  2. dry with materialdried (Na2SO4)
  3. customthe solvent removed in is vacuo
  4. customPurification (SiO2 chromatography eluting with 30-50% EtOAc in DCM)

출처 및 근거

ORD 기록
ord-5900c9177f734e8ab7dbd2fc49babfb3
출처 데이터셋
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08299246B2

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