Piperidine → cis-N-{[2-chloro-4-(1-piperidinyl)phenyl]methyl}-3-{[4-methyl-6-(methylamino)-1,3,5-triazin-2-yl]amino}cyclohexanecarboxamide

HRID 1922029

반응식

HRID 1922029 반응식
C(=O)([O-])[O-].[Cs+].[Cs+].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.Br[C:54]1[CH:59]=[CH:58][C:57]([CH2:60][NH:61][C:62]([CH:64]2[CH2:69][CH2:68][CH2:67][CH:66]([NH:70][C:71]3[N:76]=[C:75]([CH3:77])[N:74]=[C:73]([NH:78][CH3:79])[N:72]=3)[CH2:65]2)=[O:63])=[C:56]([Cl:80])[CH:55]=1.[NH:81]1[CH2:86][CH2:85][CH2:84][CH2:83][CH2:82]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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[Cl:80][C:56]1[CH:55]=[C:54]([N:81]2[CH2:86][CH2:85][CH2:84][CH2:83][CH2:82]2)[CH:59]=[CH:58][C:57]=1[CH2:60][NH:61][C:62]([C@H:64]1[CH2:69][CH2:68][CH2:67][C@@H:66]([NH:70][C:71]2[N:76]=[C:75]([CH3:77])[N:74]=[C:73]([NH:78][CH3:79])[N:72]=2)[CH2:65]1)=[O:63]

참가 물질

7

반응물 4

HCID 8082PiperidineHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 67493540N-[(4-bromo-2-chlorophenyl)methyl]-3-{[4-methyl-6-(methylamino)-1,3,5-triazin-2-yl]amino}cyclohexanecarboxamide

생성물 1

HCID 67493595cis-N-{[2-chloro-4-(1-piperidinyl)phenyl]methyl}-3-{[4-methyl-6-(methylamino)-1,3,5-triazin-2-yl]amino}cyclohexanecarboxamide

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

In a microwave reaction vessel was added cesium carbonate (0.049 g, 0.150 mmol) under nitrogen. Next, Pd2(dba)3 (4.89 mg, 5.34 μmol), BINAP (4.99 mg, 8.02 μmol), N-[(4-bromo-2-chlorophenyl)methyl]-3-{[4-methyl-6-(methylamino)-1,3,5-triazin-2-yl]amino}cyclohexanecarboxamide (0.050 g, 0.107 mmol) and piperidine (10.58 μl, 0.107 mmol) were then added to the reaction vial. Toluene (4.00 ml) was added and the reaction was heated to 100° C. for 16 hours. LCMS showed the formation of the desired product and the consumption of the starting materials. The reaction was cooled, the solvent was removed under vacuum, and the residue was purified by preparative HPLC to provide cis-N-{[2-chloro-4-(1-piperidinyl)phenyl]methyl}-3-{[4-methyl-6-(methylamino)-1,3,5-triazin-2-yl]amino}cyclohexanecarboxamide (19 mg, 0.032 mmol, 30%). MS (ES+): m/e 472, 474 [M+H]+.

후처리

  1. customIn a microwave reaction vessel

출처 및 근거

ORD 기록
ord-cde7dcf144ea4f8289a022689964ea5f
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173805B2

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