HRID2201153

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID11375

3-Aminoquinoline

C9H8N2

结构：CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21

HCID636044

1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)

C39H32OP2

HCID23681143

Sodium phenoxide--water (1/1/3)

C6H11NaO4

HCID86666167

未命名化合物

PRODUCTS

生成物

结构：N#Cc1cc(F)c(NC2(C(N)=O)CCCC2)nc1Nc1cnc2ccccc2c1

HCID67509781

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

结构：O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Pd].[Pd]

催化剂HCID9811564

Bis(dibenzylideneacetone)palladium

C51H42O3Pd2

溶剂HCID31275

1,4-Dioxane

C4H8O2

PROCEDURE

实验过程

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.

WORKUP

后处理

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

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-ec5935e9e8bd40d2849ab8388e06458d
来源数据集: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09359375B2
来源说明: uspto-grants-2016_06

反应 SMILES

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]