N,N'-Dimethylethylenediamine → methyl 4-{1-hydroxy-1-[1-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1H-pyrazol-4-yl]ethyl}benzoate

HRID 595300

반응식

HRID 595300 반응식
[OH:1][C:2]([C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=1)([C:4]1[CH:5]=[N:6][NH:7][CH:8]=1)[CH3:3].Br[C:20]1[CH:21]=[C:22]([NH:27][C:28]2[N:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[CH:30][N:29]=2)[CH:23]=[C:24]([CH3:26])[CH:25]=1.CNCCNC.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C(OCC)(=O)C.[Cu]I>[OH:1][C:2]([C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=1)([C:4]1[CH:5]=[N:6][N:7]([C:20]2[CH:21]=[C:22]([NH:27][C:28]3[N:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[CH:30][N:29]=3)[CH:23]=[C:24]([CH3:26])[CH:25]=2)[CH:8]=1)[CH3:3]

참가 물질

8

반응물 4

HCID 8070N,N'-DimethylethylenediamineHCID 10796Cesium carbonateHCID 58456396N-(3-bromo-5-methylphenyl)-4-(trifluoromethyl)pyrimidin-2-amineHCID 118208644methyl 4-[1-hydroxy-1-(1H-pyrazol-4-yl)ethyl]benzoate

생성물 1

HCID 118208752methyl 4-{1-hydroxy-1-[1-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1H-pyrazol-4-yl]ethyl}benzoate

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

반응 조건

온도
130 °C

실험 절차

A mixture of methyl 4-[1-hydroxy-1-(1H-pyrazol-4-yl)ethyl]benzoate (17 mg, 0.053 mmol), N-(3-bromo-5-methylphenyl)-4-(trifluoromethyl)pyrimidin-2-amine (13 mg, 0.053 mmol), copper(I) iodide (1 mg, 0.005 mmol), N1,N2-dimethylethane-1,2-diamine (0.47 mg, 0.005 mmol), and cesium carbonate (52 mg, 0.16 mmol) in 1,4-dioxane (2 mL) was stirred at 130° C. for 50 minutes. After being cooled to room temperature, the mixture was diluted with ethyl acetate and washed with brine. The organic layer was concentrated and the residue was purified by preparative thin layer chromatography to afford methyl 4-{1-hydroxy-1-[1-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1H-pyrazol-4-yl]ethyl}benzoate. MS ESI calc'd. for C25H23F3N5O3 [M+H]+ 498. found 498. 1H NMR (400 MHz, CDCl3): δ 8.66 (s, 1H), 8.02-8.06 (m, 3H), 7.78 (s, 1H), 7.59-7.63 (m, 3H), 7.51 (s, 1H), 7.18 (s, 1H), 7.06 (s, 1H), 3.92 (s, 3H), 3.79 (s, 1H), 3.49 (s, 1H), 2.41 (s, 3H), 1.97 (s, 3H).

후처리

  1. temperatureAfter being cooled to room temperature
  2. washwashed with brine
  3. concentrationThe organic layer was concentrated
  4. customthe residue was purified by preparative thin layer chromatography

출처 및 근거

ORD 기록
ord-597e17d7e95e49f48fbef0c8a75fcbae
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242984B2

연결된 노트

불러오는 중…