Dimethylformamide → 5-Methyl-N-{5-[4-(morpholin-4-yl)cyclohex-1-en-1-yl]pyrazin-2-yl}-1-[5-(trifluoromethyl)-pyridin-2-yl]-1H-pyrazole-4-carboxamide

HRID 1748665노트

반응식

HRID 1748665 반응식
Br[C:2]1[N:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[CH:12]=[N:13][N:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][N:18]=3)[C:15]=2[CH3:16])=[O:10])=[N:6][CH:7]=1.CC1(C)C(C)(C)OB([C:35]2[CH2:40][CH2:39][CH:38]([N:41]3[CH2:46][CH2:45][O:44][CH2:43][CH2:42]3)[CH2:37][CH:36]=2)O1.C(=O)([O-])[O-].[Na+].[Na+].CN(C)C=O>O1CCOCC1.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[CH3:16][C:15]1[N:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][N:18]=2)[N:13]=[CH:12][C:11]=1[C:9]([NH:8][C:5]1[CH:4]=[N:3][C:2]([C:35]2[CH2:40][CH2:39][CH:38]([N:41]3[CH2:42][CH2:43][O:44][CH2:45][CH2:46]3)[CH2:37][CH:36]=2)=[CH:7][N:6]=1)=[O:10]

참가 물질

8

반응물 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 592386904-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-en-1-yl)morpholineHCID 86692610N-(5-bromopyrazin-2-yl)-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide

생성물 1

HCID 866926095-Methyl-N-{5-[4-(morpholin-4-yl)cyclohex-1-en-1-yl]pyrazin-2-yl}-1-[5-(trifluoromethyl)-pyridin-2-yl]-1H-pyrazole-4-carboxamide수율 44.1%

시약·촉매·용매 3

HCID 178419050HCID 178419050, 화합물촉매HCID 962Water용매HCID 312751,4-Dioxane용매

반응 조건

온도
90 °C

실험 절차

A mixture of N-(5-bromopyrazin-2-yl)-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide (300 mg), 4-[4-(4,4,5,5-tetramethyl[1,3,2] dioxaborolan-2-yl)cyclohex-3-en-1-yl]morpholin (185 mg), tetrakis(trophenylphosphine)palladium (0) (81 mg) and sodium carbonate (186 mg) in 1,4-dioxane (7.0 ml) was stirred at 90° C. for four hours. Then, N,N-dimethylformamide (7.0 ml) and bis(diphenylphosphine)ferrocenepalladium (II) dichloride dichloromethane adduct (57 mg) were added at room temperature and stirred at 90° C. for five hours. After completion of the reaction, the reaction solution was cooled to room temperature, water was added, and the precipitated solid was collected by filtration. The resulting residue was purified with silica gel column chromatography (chloroform/methanol) twice to give the titled compound (143 mg) as a white solid.

후처리

  1. stirringstirred at 90° C. for five hours
  2. customAfter completion of the reaction
  3. temperaturethe reaction solution was cooled to room temperature
  4. filtrationthe precipitated solid was collected by filtration
  5. customThe resulting residue was purified with silica gel column chromatography (chloroform/methanol) twice

출처 및 근거

ORD 기록
ord-a7ac70f53baf4ac9a4506db65c9e35ed
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150555B2

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