Triethylamine → N-(1-((1,5-dimethyl-1H-pyrazol-3-yl)methyl)-3-ethyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79374

반응식

HRID 79374 반응식
[N:1]1[CH:2]=[C:3]([C:10]([OH:12])=O)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.ClC1C=C(Cl)C=C(Cl)C=1C(Cl)=O.C(N(CC)CC)C.[CH3:32][N:33]1[C:37]([CH3:38])=[CH:36][C:35]([CH2:39][N:40]2[C:48]3[CH:47]=[CH:46][CH:45]=[C:44]([NH2:49])[C:43]=3[C:42]([CH2:50][CH3:51])=[N:41]2)=[N:34]1>CN1C(=O)CCC1.[OH-].[Na+].CCOC(C)=O>[CH3:32][N:33]1[C:37]([CH3:38])=[CH:36][C:35]([CH2:39][N:40]2[C:48]3[C:43](=[C:44]([NH:49][C:10]([C:3]4[N:4]5[CH:9]=[CH:8][CH:7]=[CH:6][C:5]5=[N:1][CH:2]=4)=[O:12])[CH:45]=[CH:46][CH:47]=3)[C:42]([CH2:50][CH3:51])=[N:41]2)=[N:34]1

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 73142Imidazo(1,2-a)pyridine-3-carboxylic acidHCID 27337032,4,6-Trichlorobenzoyl chlorideHCID 672600441-((1,5-dimethyl-1H-pyrazol-3-yl)methyl)-3-ethyl-1H-indazol-4-amine

생성물 1

HCID 67260401N-(1-((1,5-dimethyl-1H-pyrazol-3-yl)methyl)-3-ethyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide수율 45.5%

시약·촉매·용매 3

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

반응 조건

온도
87 °C

실험 절차

To a suspension of imidazo[1,2-a]pyridine-3-carboxylic acid (45.1 mg, 0.278 mmol) in NMP (5 mL) was added 2,4,6-trichlorobenzoyl chloride (43.5 μL, 0.278 mmol) and triethylamine (38.8 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 to the reaction mixture, which was heated to 87° C. for 3 hours. The 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, then concentrated under reduced pressure. The residue was triturated with Et2O to give final product (35 mg). MS (ES+APCI) m/z=414 (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-5c291f1084824f80a87d572847174367
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841455B2

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