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

HRID 1268739ノート

反応式

HRID 1268739 の反応式
[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

参加物

6

反応物 3

HCID 516892Sodium BicarbonateHCID 17862984HCID 17862984、化合物HCID 185485896-Chloropyridine-3-carbonyl chloride--hydrogen chloride (1/1)

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
80 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-e9166156b8a941618c1abb54a1f342b6
出典データセット
uspto-grants-2007_04
特許番号
US07199124B2

反応ノート

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