2,4,6-Trichlorobenzoyl chloride → N-(1-((1,5-dimethyl-1H-pyrazol-3-yl)methyl)-3-ethyl-1H-indazol-4-yl)-7-(2-(4-methylpiperazin-1-yl)ethoxy)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79376

반응식

HRID 79376 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-:22])=O)=[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.[CH3:36][N:37]1[C:41]([CH3:42])=[CH:40][C:39]([CH2:43][N:44]2[C:52]3[CH:51]=[CH:50][CH:49]=[C:48]([NH2:53])[C:47]=3[C:46]([CH2:54][CH3:55])=[N:45]2)=[N:38]1>CN1C(=O)CCC1.[OH-].[Na+].CCOC(C)=O>[CH3:36][N:37]1[C:41]([CH3:42])=[CH:40][C:39]([CH2:43][N:44]2[C:52]3[C:47](=[C:48]([NH:53][C:20]([C:17]4[N:14]5[CH:15]=[CH:16][C:11]([O:10][CH2:9][CH2:8][N:5]6[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]6)=[CH:12][C:13]5=[N:19][CH:18]=4)=[O:22])[CH:49]=[CH:50][CH:51]=3)[C:46]([CH2:54][CH3:55])=[N:45]2)=[N:38]1

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 672600441-((1,5-dimethyl-1H-pyrazol-3-yl)methyl)-3-ethyl-1H-indazol-4-amine

생성물 1

HCID 67261556N-(1-((1,5-dimethyl-1H-pyrazol-3-yl)methyl)-3-ethyl-1H-indazol-4-yl)-7-(2-(4-methylpiperazin-1-yl)ethoxy)imidazo[1,2-a]pyridine-3-carboxamide수율 68.7%

시약·촉매·용매 3

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

반응 조건

온도
87 °C

실험 절차

To a solution of lithium 7-(2-(4-methylpiperazin-1-yl)ethoxy)imidazo[1,2-a]pyridine-3-carboxylate (89.1 mg, 0.278 mmol) in NMP (6 mL) at 0° C. was added 2,4,6-trichlorobenzoyl chloride (43.5 μL, 0.278 mmol). The reaction mixture was stirred for 30 minutes. 1-((1,5-Dimethyl-1H-pyrazol-3-yl)methyl)-3-ethyl-1H-indazol-4-amine (50 mg, 0.186 mmol) was added and the mixture was heated at 87° C. for 3 hours. The reaction mixture was cooled to ambient temperature, and diluted with 10% NaOH aqueous solution (5 mL) and EtOAc (20 mL). The organic phase was washed with water and brine and then concentrated under reduced pressure. The residue was triturated with Et2O to give final product (71 mg). MS (ES+APCI) m/z=556 (M+H).

후처리

  1. temperatureThe reaction 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-bd91e1da63934e00a5e45de0438dd907
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841455B2

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