Cesium carbonate → HCID 89923413, 화합물

HRID 921930노트

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HRID 921930 반응식
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

참가 물질

8

반응물 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, 화합물

생성물 1

HCID 89923413HCID 89923413, 화합물수율 62%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 312751,4-Dioxane용매

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온도
90 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-dd4b93acbaa54b6bb11ed1e98daeb8ac
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273057B2

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