Cesium carbonate → 5'-Methoxy-N,2'-dimethyl-4'-(4-(5-methyl-1H-pyrazol-3-ylamino)-5-(trifluoromethyl)pyrimidin-2-ylamino)biphenyl-4-carboxamide

HRID 2091952노트

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HRID 2091952 반응식
Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=[C:4]([NH:12][C:13]2[C:18]([O:19][CH3:20])=[CH:17][C:16]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([NH:29][CH3:30])=[O:28])=[CH:23][CH:22]=3)=[C:15]([CH3:31])[CH:14]=2)[N:3]=1.[CH3:32][C:33]1[NH:37][N:36]=[C:35]([NH2:38])[CH:34]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:20][O:19][C:18]1[C:13]([NH:12][C:4]2[N:3]=[C:2]([NH:38][C:35]3[CH:34]=[C:33]([CH3:32])[NH:37][N:36]=3)[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=2)=[CH:14][C:15]([CH3:31])=[C:16]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([NH:29][CH3:30])=[O:28])=[CH:23][CH:22]=2)[CH:17]=1

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 931461H-Pyrazol-3-amine, 5-methyl-HCID 866477934'-(4-Chloro-5-(trifluoromethyl)pyrimidin-2-ylamino)-5'-methoxy-N,2'-dimethylbiphenyl-4-carboxamide

생성물 1

HCID 252654055'-Methoxy-N,2'-dimethyl-4'-(4-(5-methyl-1H-pyrazol-3-ylamino)-5-(trifluoromethyl)pyrimidin-2-ylamino)biphenyl-4-carboxamide

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 8028Tetrahydrofuran용매

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온도
150 °C

실험 절차

The mixture of 4′-(4-chloro-5-(trifluoromethyl)pyrimidin-2-ylamino)-5′-methoxy-N,2′-dimethylbiphenyl-4-carboxamide (Step 1, 20 mg, 0.044 mmol), 5-methyl-1H-pyrazol-3-amine (4.3 mg, 0.044 mmol), Xantophos (5.0 mg, 0.009 mmol), paladium acetate (II) (1.0 mg, 0.004 mmol), and cesium carbonate (28.6 mg, 0.088 mmol) in 2.0 mL of THF is heated at 150° C. in a microwave reactor for 25 min. The reaction mixture is filtered, the filtrate is concentrated in vacuo, and purified by preparative RP-HPLC to afford 5′-Methoxy-N,2′-dimethyl-4′-(4-(5-methyl-1H-pyrazol-3-ylamino)-5-(trifluoromethyl)pyrimidin-2-ylamino)biphenyl-4-carboxamide; ESMS m/z 512.2 (M+H+).

후처리

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe filtrate is concentrated in vacuo
  3. custompurified by preparative RP-HPLC

출처 및 근거

ORD 기록
ord-d742f89beaf64013b725ebc242cc6066
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08440681B2

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