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3-Aminoquinoline → 1-(5-Cyano-3-fluoro-6-(quinolin-3-ylamino)pyridin-2-ylamino)cyclopentanecarboxamide

HRID 84921
ノート
印刷プレビュー

反応式

HRID 84921 の反応式
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2([C:14]([NH2:16])=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10]2)[C:5]([F:17])=[CH:4][C:3]=1[C:18]#[N:19].[NH2:20][C:21]1[CH:22]=[N:23][C:24]2[C:29]([CH:30]=1)=[CH:28][CH:27]=[CH:26][CH:25]=2.O.O.O.[O-]C1C=CC=CC=1.[Na+].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>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:18]([C:3]1[CH:4]=[C:5]([F:17])[C:6]([NH:8][C:9]2([C:14]([NH2:16])=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10]2)=[N:7][C:2]=1[NH:20][C:21]1[CH:22]=[N:23][C:24]2[C:29]([CH:30]=1)=[CH:28][CH:27]=[CH:26][CH:25]=2)#[N:19]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 113753-AminoquinolineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23681143Sodium Phenoxide TrihydrateHCID 866661671-(6-Chloro-5-cyano-3-fluoropyridin-2-ylamino)cyclopentanecarboxamide

生成物 1

HCID 675097811-(5-Cyano-3-fluoro-6-(quinolin-3-ylamino)pyridin-2-ylamino)cyclopentanecarboxamide

試薬・触媒・溶媒

2
HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

実験手順

A mixture of 1-(6-chloro-5-cyano-3-fluoropyridin-2-ylamino)cyclopentanecarboxamide (90 mg, 0.318 mmol), 3-aminoquinoline (58 mg, 0.402 mmol), sodium phenoxide trihydrate (85 mg, 0.500 mmol), xantphos (30 mg, 0.051 mmol) and Pd2 dba3 (20 mg, 0.021 mmol) in dioxane (2 mL) was degassed with Ar, then was stirred at 110 C for 4 h. Water and EtOAc were added. The organic phase was washed with aq. 1N NaOH, dried over Na2SO4, concentrated in vacuo to give crude 1-(5-cyano-3-fluoro-6-(quinolin-3-ylamino)pyridin-2-ylamino)cyclopentanecarboxamide.

後処理

  1. customwas degassed with Ar
  2. additionWater and EtOAc were added
  3. washThe organic phase was washed with aq. 1N NaOH
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-32c07895909e4870bbc7b369a156f02c
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08846928B2

反応ノート

読み込み中…

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