Trifluoroacetic acid → cis-3-(1H-indazol-5-ylamino)-5-(2-aminocyclohexylamino)pyrazine-2-carboxamide

HRID 332809

반응식

HRID 332809 반응식
[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

참가 물질

7

반응물 4

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 3429171,2-Diaminocyclohexane, cis-HCID 866856023-(1H-indazol-5-ylamino)-5-chloropyrazine-2-carboxamide

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
150 °C

실험 절차

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.

후처리

  1. temperatureThe reaction mixture was cooled

출처 및 근거

ORD 기록
ord-a19ccca8d35144f0804de074e685fe15
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877760B2

연결된 노트

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