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Cesium carbonate → HCID 89922864, 화합물

HRID 921831
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HRID 921831 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:39])=[CH:29][C:30]([CH2:35][CH2:36][CH2:37][OH:38])=[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:39][C:28]1[CH:29]=[C:30]([CH2:35][CH2:36][CH2:37][OH:38])[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: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
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

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 89923055HCID 89923055, 화합물

생성물 1

HCID 89922864HCID 89922864, 화합물수율 80.4%

시약·촉매·용매 3

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

반응 조건

온도
100 °C

실험 절차

2-chloro-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (211 mg, 0.595 mmol), 5-amino-4-chloro-2-(3-hydroxypropyl)benzonitrile (125 mg, 0.595 mmol), palladium (II) acetate (40.1 mg, 0.178 mmol), DPPF (33.0 mg, 0.059 mmol), Xantphos (34.4 mg, 0.059 mmol), and cesium carbonate (388 mg, 1.189 mmol) were combined in a 20 dram vial and dioxane (6 mL) was added. The vial was evacuated and backfilled with N2 3×, then heated at 100° C. for 30 min. 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 (0-3% MeOH/DCM; 12 g column). 2-((2-chloro-5-cyano-4-(3-hydroxypropyl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (253 mg) was obtained as a yellow glass.

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 (0-3% MeOH/DCM; 12 g column)

출처 및 근거

ORD 기록
ord-a30c4960c0164c63ac2ff2fa76e52a21
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09273057B2

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