Diisopropylethylamine → (S)-methyl 3-(4-(2-(4-(4-cyano-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridin-6-yl)-2-(trifluoro-methyl)phenoxy)ethyl)piperidin-1-yl)-2-hydroxypropanoate

HRID 517996

반응식

HRID 517996 반응식
[O:1]1[CH2:3][C@H:2]1[C:4]([O:6][CH3:7])=[O:5].FC(F)(F)C(O)=O.[CH3:15][N:16]1[C:24]2[CH:23]=[C:22]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][CH:34]4[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]4)=[C:27]([C:40]([F:43])([F:42])[F:41])[CH:26]=3)[N:21]=[C:20]([C:44]#[N:45])[C:19]=2[N:18]=[N:17]1.CCN(C(C)C)C(C)C>CO>[C:44]([C:20]1[C:19]2[N:18]=[N:17][N:16]([CH3:15])[C:24]=2[CH:23]=[C:22]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][CH:34]3[CH2:35][CH2:36][N:37]([CH2:3][C@H:2]([OH:1])[C:4]([O:6][CH3:7])=[O:5])[CH2:38][CH2:39]3)=[C:27]([C:40]([F:42])([F:43])[F:41])[CH:26]=2)[N:21]=1)#[N:45]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 10942355Methyl (2S)-2-oxiranecarboxylateHCID 866733471-methyl-6-(4-(2-(piperidin-4-yl)ethoxy)-3-(trifluoromethyl)phenyl)-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile 2,2,2-trifluoroacetate

생성물 1

HCID 70945180(S)-methyl 3-(4-(2-(4-(4-cyano-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridin-6-yl)-2-(trifluoro-methyl)phenoxy)ethyl)piperidin-1-yl)-2-hydroxypropanoate

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

(S)-Methyl oxirane-2-carboxylate (1.837 mmol, 0.188 g), 1-methyl-6-(4-(2-(piperidin-4-yl)ethoxy)-3-(trifluoromethyl)phenyl)-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile 2,2,2-trifluoroacetate (0.918 mmol, 0.5 g) and Hunig's base (1.837 mmol, 0.304 ml, 0.237 g) were heated in Methanol (5 ml) to 100° C. for 10 minutes in the microwave. The reaction mixture was concentrated in vacuo. The resulting residue was purified by column chromatography, eluting with DCM—90/10 DCM/MeOH to afford (S)-methyl 3-(4-(2-(4-(4-cyano-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridin-6-yl)-2-(trifluoro-methyl)phenoxy)ethyl)piperidin-1-yl)-2-hydroxypropanoate. (0.34 g)

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe resulting residue was purified by column chromatography
  3. washeluting with DCM—90/10 DCM/MeOH

출처 및 근거

ORD 기록
ord-508742002a5048a8a5f69143c92b5a7d
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115126B2

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