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Sodium Hydroxide → (S)-4-(5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)pyrimidin-2-yl)-2-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)morpholine

HRID 1478568
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HRID 1478568 반응식
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:12]=[C:11]3[N:13]([CH2:16][C@@H:17]4[CH2:22][N:21]([C:23]5[N:28]=[CH:27][C:26]([C:29]6[CH2:34][CH2:33][N:32]([C:35](OC(C)(C)C)=O)[CH2:31][CH:30]=6)=[CH:25][N:24]=5)[CH2:20][CH2:19][O:18]4)[N:14]=[N:15][C:10]3=[N:9][CH:8]=2)[CH:4]=[N:3]1.[OH-].[Na+]>C=O.C(O)(=O)C>[CH3:35][N:32]1[CH2:31][CH:30]=[C:29]([C:26]2[CH:27]=[N:28][C:23]([N:21]3[CH2:20][CH2:19][O:18][C@H:17]([CH2:16][N:13]4[C:11]5=[N:12][C:7]([C:5]6[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=6)=[CH:8][N:9]=[C:10]5[N:15]=[N:14]4)[CH2:22]3)=[N:24][CH:25]=2)[CH2:34][CH2:33]1
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참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 118364759(S)-tert-butyl 4-(2-(2-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)morpholino)pyrimidin-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate

생성물 1

HCID 73504290(S)-4-(5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)pyrimidin-2-yl)-2-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)morpholine수율 59.5%

시약·촉매·용매 2

HCID 176
Acetic Acid
용매
HCID 712Formaldehyde용매

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온도
95 °C

실험 절차

(S)-tert-butyl 4-(2-(2-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)morpholino)pyrimidin-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate (36 mg, 0.06 mmol) was dissolved in 35% HCHO (0.1 ml) and acetic acid (0.5 ml), followed by stirring at 95° C. overnight. After the completion of the reaction, the reaction mixture was adjusted to pH 11-12 with NaOH (aq.), and extracted with H2O and EA, followed by drying (Na2SO4), filtration and concentration under reduced pressure, and the residue was purified by column chromatography (MeOH:MC=1:10), to give (S)-4-(5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)pyrimidin-2-yl)-2-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)morpholine (16.9 mg, 56%).

후처리

  1. customAfter the completion of the reaction
  2. extractionextracted with H2O and EA
  3. customby drying
  4. filtration(Na2SO4), filtration and concentration under reduced pressure
  5. customthe residue was purified by column chromatography (MeOH:MC=1:10)

출처 및 근거

ORD 기록
ord-e9942982e06b407d8dc662e01ecfeb5d
출처 데이터셋
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09403831B2

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