三氟乙酸 → cis-3-(1H-indazol-5-ylamino)-5-(2-aminocyclohexylamino)pyrazine-2-carboxamide

HRID 332809

反应方程式

HRID 332809 反应方程式
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][C:11]3[C:12]([C:18]([NH2:20])=[O:19])=[N:13][CH:14]=[C:15](Cl)[N:16]=3)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.CCN(C(C)C)C(C)C.[C@@H:30]1([NH2:37])[CH2:35][CH2:34][CH2:33][CH2:32][C@@H:31]1[NH2:36].C(O)(C(F)(F)F)=O>CN1C(=O)CCC1.O>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][C:11]3[C:12]([C:18]([NH2:20])=[O:19])=[N:13][CH:14]=[C:15]([NH:36][C@@H:31]4[CH2:32][CH2:33][CH2:34][CH2:35][C@@H:30]4[NH2:37])[N:16]=3)=[CH:7][CH:8]=2)[CH:3]=[N:2]1

参与物

7

反应物 4

HCID 6422三氟乙酸HCID 81531N,N-二异丙基乙胺HCID 342917顺式-1,2-环己二胺HCID 866856023-(1H-indazol-5-ylamino)-5-chloropyrazine-2-carboxamide

产物 1

HCID 86685601cis-3-(1H-indazol-5-ylamino)-5-(2-aminocyclohexylamino)pyrazine-2-carboxamide

试剂、催化剂与溶剂 2

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 13387N-甲基吡咯烷酮溶剂

反应条件

温度
150 °C

实验过程

To 3-(1H-indazol-5-ylamino)-5-chloropyrazine-2-carboxamide (˜100 mg) in ˜3 mL NMP was added 6 equivalents of DIEA and 20 equivalents of racemic cis-1,2-cyclohexanediamine. The mixture was heated at 150° C. in a sealed tube overnight. The reaction mixture was cooled, acidified with TFA, diluted with water and prepped via rpHPLC to give the title compound. MS found for C18H22N8O as (M+H)+ 367.2.

后处理

  1. temperatureThe reaction mixture was cooled

来源与证据

ORD记录
ord-a19ccca8d35144f0804de074e685fe15
来源数据集
uspto-grants-2014_11
专利号
US08877760B2

关联笔记

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