HRID2200423

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID11430

Potassium Carbonate

CK2O3

HCID13396

Benzonitrile, 4-amino-

C7H6N2

结构：c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1

HCID634876

2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl

C44H32P2

结构：CC(C)(C)OC(=O)N[C@H]1CCCC[C@H]1Nc1cnc(C#N)c(Cl)n1

HCID86685544

未命名化合物

PRODUCTS

生成物

结构：CC(C)(C)OC(=O)N[C@H]1CCCC[C@H]1Nc1cnc(C#N)c(Nc2ccc(C#N)cc2)n1

HCID86685553

未命名化合物

收率 149.6%

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID167845

Diacetatopalladium

C4H6O4Pd

溶剂HCID31275

1,4-Dioxane

C4H8O2

PROCEDURE

实验过程

A mixture of tert-butyl (1S,2R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)cyclohexylcarbamate (90 mg, 0.256 mmol), 4-aminobenzonitrile (42 mg, 0.355 mmol), K2CO3 (100 mg, 0.724 mmol), BINAP (30 mg, 0.048 mmol) and Pd(OAc)2 (15 mg, 0.066 mmol) in dioxane (2 mL) was degassed with Ar, then was stirred at 110 C for 20 h. Water and EtOAc were added. Organic phase was separated, dried over Na2SO4, concentrated in vacuo to give a crude tert-butyl (1S,2R)-2-(5-cyano-6-(4-cyanophenylamino)pyrazin-2-ylamino)cyclohexylcarbamate (166 mg).

WORKUP

后处理

customwas degassed with Ar
additionWater and EtOAc were added
customOrganic phase was separated
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-2a9edf7195d0423c81ce295bd4767e1f
来源数据集: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09359308B2
来源说明: uspto-grants-2016_06

反应 SMILES

Cl[C:2]1[N:7]=[C:6]([NH:8][C@@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]2[NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH:5]=[N:4][C:3]=1[C:23]#[N:24].[NH2:25][C:26]1[CH:33]=[CH:32][C:29]([C:30]#[N:31])=[CH:28][CH:27]=1.C([O-])([O-])=O.[K+].[K+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:23]([C:3]1[N:4]=[CH:5][C:6]([NH:8][C@@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]2[NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[N:7][C:2]=1[NH:25][C:26]1[CH:33]=[CH:32][C:29]([C:30]#[N:31])=[CH:28][CH:27]=1)#[N:24]