Cesium carbonate → 6-Chloro-N-(5-(4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-yl)-[1,2,4]-triazolo[1,5-a]pyridin-8-amine

HRID 1024036노트

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HRID 1024036 반응식
Br[C:2]1[C:3]2[N:4]([N:9]=[CH:10][N:11]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[O:12]1[CH2:15][CH:14]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:23]=[CH:24][C:25]([NH2:28])=[N:26][CH:27]=3)[CH2:18][CH2:17]2)[CH2:13]1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>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].O1CCOCC1>[Cl:8][C:6]1[CH:7]=[C:2]([NH:28][C:25]2[CH:24]=[CH:23][C:22]([N:19]3[CH2:20][CH2:21][N:16]([CH:14]4[CH2:13][O:12][CH2:15]4)[CH2:17][CH2:18]3)=[CH:27][N:26]=2)[C:3]2[N:4]([N:9]=[CH:10][N:11]=2)[CH:5]=1

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 866841255-(4-(Oxetan-3-yl)piperazin-1-yl)pyridin-2-amineHCID 866841358-Bromo-6-chloro-(1,2,4)triazolo(1,5-a)pyridine

생성물 1

HCID 866841346-Chloro-N-(5-(4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-yl)-[1,2,4]-triazolo[1,5-a]pyridin-8-amine수율 64.8%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매

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온도
105 °C

실험 절차

A 25-mL single-neck round-bottomed flask equipped with a magnetic stirrer and reflux condenser was charged with 1,4-dioxane (8 mL), 108c (250 mg, 1.07 mmol), 5-(4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-amine (252 mg, 1 mmol), and cesium carbonate (700 mg, 2 mmol). Xantphos (30 mg, 0.08 mmol) and Pd2(dba)3 (55 mg, 0.08 mmol) were added, and the reaction mixture was heated at 105° C. for 3 h. After this time the reaction was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel chromatography eluting with CH2Cl2/MeOH (20:1) to afford 108d (250 mg, 60%). MS: [M+H]+ 386.

후처리

  1. customA 25-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. temperaturereflux condenser
  3. temperatureAfter this time the reaction was cooled to room temperature
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by silica gel chromatography
  7. washeluting with CH2Cl2/MeOH (20:1)

출처 및 근거

ORD 기록
ord-e3337a395ce544a1b057cdf948eaa7bd
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722676B2

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