Sodium Bicarbonate → 6-CHLORO-N-[5-(2-CYCLOPENTYLAMINO-4-PYRIDYL)-4-(3-METHYLPHENYL)-1,3-THIAZOL-2-YL]NICOTINAMIDE

HRID 1268739노트

반응식

HRID 1268739 반응식
[CH:1]1([NH:6][C:7]2[CH:12]=[C:11]([C:13]3[S:17][C:16]([NH2:18])=[N:15][C:14]=3[C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[CH:20]=3)[CH:10]=[CH:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[Cl:27][C:28]1[CH:36]=[CH:35][C:31]([C:32](Cl)=[O:33])=[CH:30][N:29]=1.C(=O)([O-])O.[Na+]>CN(C)C1C=CN=CC=1.CN(C)C(=O)C>[Cl:27][C:28]1[CH:36]=[CH:35][C:31]([C:32]([NH:18][C:16]2[S:17][C:13]([C:11]3[CH:10]=[CH:9][N:8]=[C:7]([NH:6][CH:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)[CH:12]=3)=[C:14]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[CH:20]=3)[N:15]=2)=[O:33])=[CH:30][N:29]=1

참가 물질

6

반응물 3

HCID 516892Sodium BicarbonateHCID 17862984HCID 17862984, 화합물HCID 185485896-Chloropyridine-3-carbonyl chloride--hydrogen chloride (1/1)

생성물 1

HCID 102066296-CHLORO-N-[5-(2-CYCLOPENTYLAMINO-4-PYRIDYL)-4-(3-METHYLPHENYL)-1,3-THIAZOL-2-YL]NICOTINAMIDE수율 43.7%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 31374Dimethylacetamide용매

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온도
80 °C

실험 절차

To a solution of [5-(2-cyclopentylamino-4-pyridyl)-4-(3-methylphenyl)-1,3-thiazol-2-yl]amine (0.50 g, 1.4 mmol) and 4-dimethylaminopyridine (0.052 g, 0.43 mmol) in N,N-dimethylacetamide (10 mL) was added 6-chloronicotinoyl chloride hydrochloride (0.46 g, 2.1 mmol), and the mixture was stirred at 80° C. for 14 hrs. Into the reaction mixture was poured aqueous sodium hydrogen carbonate solution and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried and concentrated. The residue was purified by silica gel column chromatography (hexane-ethyl acetate 4:1) and the resulting crystals were recrystallized from ethanol to give the title compound (0.30 g, yield 42%).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate 4:1)
  6. customthe resulting crystals were recrystallized from ethanol

출처 및 근거

ORD 기록
ord-e9166156b8a941618c1abb54a1f342b6
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07199124B2

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