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

반응식

HRID 79381 반응식
[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]

참가 물질

7

반응물 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

생성물 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-carboxamide수율 66.9%

시약·촉매·용매 3

HCID 8857Ethyl Acetate용매HCID 13387N-methyl-2-pyrrolidone용매HCID 14798Sodium Hydroxide용매

반응 조건

온도
87 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-27d8cad7eea5470f956803bfcf5fb177
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841455B2

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