2,4,6-Trichlorobenzoyl chloride → N-(3-ethyl-1-((1-methyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-yl)-7-(2-(4-methylpiperazin-1-yl)ethoxy)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79381

反応式

HRID 79381 の反応式
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][N:14]3[C:17]([C:20]([O-])=[O:21])=[CH:18][N:19]=[C:13]3[CH:12]=2)[CH2:4][CH2:3]1.[Li+].ClC1C=C(Cl)C=C(Cl)C=1C(Cl)=O.[CH2:36]([C:38]1[C:46]2[C:45]([NH2:47])=[CH:44][CH:43]=[CH:42][C:41]=2[N:40]([CH2:48][C:49]2[CH:53]=[CH:52][N:51]([CH3:54])[N:50]=2)[N:39]=1)[CH3:37]>CN1C(=O)CCC1.[OH-].[Na+].CCOC(C)=O>[CH2:36]([C:38]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][C:45]=2[NH:47][C:20]([C:17]2[N:14]3[CH:15]=[CH:16][C:11]([O:10][CH2:9][CH2:8][N:5]4[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]4)=[CH:12][C:13]3=[N:19][CH:18]=2)=[O:21])[N:40]([CH2:48][C:49]2[CH:53]=[CH:52][N:51]([CH3:54])[N:50]=2)[N:39]=1)[CH3:37]

参加物

7

反応物 3

HCID 27337032,4,6-Trichlorobenzoyl chlorideHCID 67252742Lithium 7-(2-(4-methylpiperazin-1-yl)ethoxy)imidazo[1,2-a]pyridine-3-carboxylateHCID 672599453-ethyl-1-((1-methyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-amine

生成物 1

HCID 67260125N-(3-ethyl-1-((1-methyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-yl)-7-(2-(4-methylpiperazin-1-yl)ethoxy)imidazo[1,2-a]pyridine-3-carboxamide収率 66.9%

試薬・触媒・溶媒 3

HCID 8857Ethyl Acetate溶媒HCID 13387N-methyl-2-pyrrolidone溶媒HCID 14798Sodium Hydroxide溶媒

反応条件

温度
87 °C

実験手順

To a suspension of lithium 7-(2-(4-methylpiperazin-1-yl)ethoxy)imidazo[1,2-a]pyridine-3-carboxylate (94.0 mg, 0.294 mmol) (Example 56, step A) in NMP (4 mL) was added 2,4,6-trichlorobenzoyl chloride (45.9 μL, 0.294 mmol). The reaction mixture was stirred for 30 minutes. 3-Ethyl-1-((1-methyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-amine (50 mg, 0.196 mmol) was added and the mixture was heated at 87° C. for 3 hours. The mixture was cooled to ambient temperature and diluted with 10% NaOH aqueous solution (5 mL) and EtOAc. The organic phase was washed with water and brine, concentrated under reduced pressure and the residue was triturated with Et2O to give the final product (71 mg). MS (ES+APCI) m/z=542 (M+H).

後処理

  1. temperatureThe mixture was cooled to ambient temperature
  2. washThe organic phase was washed with water and brine
  3. concentrationconcentrated under reduced pressure
  4. customthe residue was triturated with Et2O

出典と根拠

ORDレコード
ord-27d8cad7eea5470f956803bfcf5fb177
出典データセット
uspto-grants-2014_09
特許番号
US08841455B2

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