Potassium Carbonate → N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79382

반응식

HRID 79382 반응식
Br[C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([NH:13][C:14]3[CH:22]=[CH:21][CH:20]=[C:19]4[C:15]=3[C:16]([CH2:31][CH3:32])=[N:17][N:18]4[CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[N:25]=3)=[O:12])=[CH:9][N:10]=[C:4]2[CH:3]=1.[N:33]1[CH:34]=[CH:35][N:36]2[CH2:41][CH2:40][N:39](C(OC(C)(C)C)=O)[CH2:38][C:37]=12.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[CH2:31]([C:16]1[C:15]2[C:19](=[CH:20][CH:21]=[CH:22][C:14]=2[NH:13][C:11]([C:8]2[N:5]3[CH:6]=[CH:7][C:2]([C:35]4[N:36]5[CH2:41][CH2:40][NH:39][CH2:38][C:37]5=[N:33][CH:34]=4)=[CH:3][C:4]3=[N:10][CH:9]=2)=[O:12])[N:18]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[N:25]=2)[N:17]=1)[CH3:32]

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 21955306tert-Butyl 5,6-dihydroimidazo(1,2-a)pyrazine-7(8H)-carboxylateHCID 672595577-Bromo-N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

생성물 1

HCID 53262090N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide수율 26.3%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 178418397HCID 178418397, 화합물촉매HCID 6228Dimethylformamide용매

반응 조건

온도
140 °C

실험 절차

7-Bromo-N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (prepared as in Example 127, Step A; 50 mg, 0.10 mmol) in DMF (4 mL) was added tert-butyl 5,6-dihydroimidazo[1,2-a]pyrazine-7(8H)-carboxylate (68 mg, 0.31 mmol), Pd(PPh3)4 (12 mg, 0.01 mmol), palladium diacetate (2.3 mg, 0.010 mmol) and K2CO3 (42 mg, 0.31 mmol). The reaction mixture was purged with argon and the reaction vial was sealed and the mixture was heated to 140° C. for 3 hours. The mixture was cooled to ambient temperature and diluted with DCM (20 mL). The solution was washed with H2O, dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by silica gel chromatography (DCM/MeOH/NH4OH 10:1:0.1) to provide the final product (14 mg). MS (ES+APCI) m/z=532 (M+H).

후처리

  1. customThe reaction mixture was purged with argon
  2. customthe reaction vial was sealed
  3. temperatureThe mixture was cooled to ambient temperature
  4. additiondiluted with DCM (20 mL)
  5. washThe solution was washed with H2O
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography (DCM/MeOH/NH4OH 10:1:0.1)

출처 및 근거

ORD 기록
ord-50c00976280348d0b5e801d60b2b650b
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841455B2

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