Cesium carbonate → HCID 89923413、化合物

HRID 921930ノート

反応式

HRID 921930 の反応式
Cl[C:2]1[N:7]=[C:6]([N:8]([CH:18]2[CH2:20][CH2:19]2)[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[C:5]2=[N:21][CH:22]=[C:23]([C:24]#[N:25])[N:4]2[N:3]=1.[NH2:26][C:27]1[C:28]([Cl:41])=[CH:29][C:30]([CH:35]([CH2:37][C:38](=[O:40])[CH3:39])[CH3:36])=[C:31]([CH:34]=1)[C:32]#[N:33].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].O1CCOCC1>[Cl:41][C:28]1[CH:29]=[C:30]([CH:35]([CH2:37][C:38](=[O:40])[CH3:39])[CH3:36])[C:31]([C:32]#[N:33])=[CH:34][C:27]=1[NH:26][C:2]1[N:7]=[C:6]([N:8]([CH:18]2[CH2:20][CH2:19]2)[CH2:9][C:10]2[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=2)[C:5]2=[N:21][CH:22]=[C:23]([C:24]#[N:25])[N:4]2[N:3]=1

参加物

8

反応物 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 867084772-Chloro-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrileHCID 89922622HCID 89922622、化合物

生成物 1

HCID 89923413HCID 89923413、化合物収率 62%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

2-chloro-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (100 mg, 0.282 mmol), 5-amino-4-chloro-2-(4-oxopentan-2-yl)benzonitrile (67 mg, 0.282 mmol), palladium (II) acetate (18.9 mg, 0.085 mmol), DPPF (15.6 mg, 0.028 mmol), Xantphos (16.3 mg, 0.028 mmol), and cesium carbonate (184 mg, 0.564 mmol) were combined in a 10 dram vial and dioxane (2 mL) was added. The vial was evacuated and backfilled with N2 3×, then heated at 90° C. for 1 h. The reaction was cooled to room temperature and the reaction mixture was filtered through celite, rinsing with EtOAc. The solvent was removed in vacuo and the material was purified by ISCO Companion (0-100% EtOAc/Hexane). 2-((2-chloro-5-cyano-4-(4-oxopentan-2yl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (97 mg) was obtained as a yellow foam.

後処理

  1. customThe vial was evacuated
  2. temperatureThe reaction was cooled to room temperature
  3. filtrationthe reaction mixture was filtered through celite
  4. washrinsing with EtOAc
  5. customThe solvent was removed in vacuo
  6. customthe material was purified by ISCO Companion (0-100% EtOAc/Hexane)

出典と根拠

ORDレコード
ord-dd4b93acbaa54b6bb11ed1e98daeb8ac
出典データセット
uspto-grants-2016_03
特許番号
US09273057B2

反応ノート

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