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Sodium Acetate → 5-(2-Amino-5-methyl-thiazol-4-yl)-6-methyl-2-oxo-1-(3-trifluoromethyl-phenyl)-1,2-dihydro-pyridine-3-carboxylic acid 4-methanesulfonyl-benzylamide

HRID 1888813
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HRID 1888813 반응식
Br[CH:2]([CH3:37])[C:3]([C:5]1[CH:6]=[C:7]([C:23]([NH:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:29][CH:28]=2)=[O:24])[C:8](=[O:22])[N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[C:10]=1[CH3:11])=O.[NH2:38][C:39]([NH2:41])=[S:40].CC([O-])=O.[Na+]>CCO>[CH3:36][S:33]([C:30]1[CH:29]=[CH:28][C:27]([CH2:26][NH:25][C:23]([C:7]2[C:8](=[O:22])[N:9]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:19])[F:20])[CH:13]=3)[C:10]([CH3:11])=[C:5]([C:3]3[N:38]=[C:39]([NH2:41])[S:40][C:2]=3[CH3:37])[CH:6]=2)=[O:24])=[CH:32][CH:31]=1)(=[O:34])=[O:35]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 517045Sodium AcetateHCID 2723790ThioureaHCID 866147825-(2-bromopropanoyl)-6-methyl-N-[4-(methylsulfonyl)benzyl]-2-oxo-1-(3-(trifluoromethyl)phenyl)-1,2-dihydropyridine-3-carboxamide

생성물 1

HCID 866147835-(2-Amino-5-methyl-thiazol-4-yl)-6-methyl-2-oxo-1-(3-trifluoromethyl-phenyl)-1,2-dihydro-pyridine-3-carboxylic acid 4-methanesulfonyl-benzylamide수율 67.3%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
90 °C

실험 절차

5-(2-Bromopropanoyl)-6-methyl-N-[4-(methylsulfonyl)benzyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide (Example 53 (b), 0.04 g, 0.067 mmol), thiourea (0.0067 g, 0.086 mmol), NaOAc (0.011 g, 0.136 mmol), EtOH (2 ml) and a magnetic stirrer bar were placed in a tube designed for microwave synthesis. The vial was sealed and the mixture was heated in a CEM Discover Microwave apparatus (100 W, 90° C.) for 20 minutes, giving complete conversion of the starting material to a single product according to LC-MS. The solvents were evaporated to give a crude mixture which was purified on preparative HPLC, giving the title compound (0.026 g, 66%) as a slightly yellowish solid after freeze-drying the pure fractions.

후처리

  1. customdesigned for microwave synthesis
  2. customThe vial was sealed
  3. customgiving complete conversion of the starting material to a single product
  4. customThe solvents were evaporated
  5. customto give a crude mixture which
  6. customwas purified on preparative HPLC

출처 및 근거

ORD 기록
ord-059c634872774036bc8e8338970ac044
출처 데이터셋
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08501784B2

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