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

HRID 2091952ノート

反応式

HRID 2091952 の反応式
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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
150 °C

実験手順

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+).

後処理

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

出典と根拠

ORDレコード
ord-d742f89beaf64013b725ebc242cc6066
出典データセット
uspto-grants-2013_05
特許番号
US08440681B2

反応ノート

読み込み中…