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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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1,4-Dioxane → Benzyl [2-[({4-[(3S,5R)-3-[(tert-butoxycarbonyl)amino]-5-(trifluoromethyl)piperidin-1-yl]pyridin-3-yl}amino)carbonyl]-7-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)quinolin-3-yl]carbamate

HRID 924479
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인쇄 미리보기

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HRID 924479 반응식
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([NH:39][C:40](=[O:49])[O:41][CH2:42][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[C:8]([C:12]([NH:14][C:15]3[CH:16]=[N:17][CH:18]=[CH:19][C:20]=3[N:21]3[CH2:26][C@H:25]([C:27]([F:30])([F:29])[F:28])[CH2:24][C@H:23]([NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:22]3)=[O:13])=[N:9]2)=[CH:4][CH:3]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O1CCOCC1.[CH3:64][N:65]1[CH2:70][CH:69]=[C:68](B2OC(C)(C)C(C)(C)O2)[CH2:67][CH2:66]1>C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.NC1C=CC=CC=1C1C=CC=CC=1[Pd]Cl.O>[C:35]([O:34][C:32]([NH:31][C@H:23]1[CH2:24][C@@H:25]([C:27]([F:29])([F:28])[F:30])[CH2:26][N:21]([C:20]2[CH:19]=[CH:18][N:17]=[CH:16][C:15]=2[NH:14][C:12]([C:8]2[C:7]([NH:39][C:40](=[O:49])[O:41][CH2:42][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)=[CH:6][C:5]3[C:10](=[CH:11][C:2]([C:68]4[CH2:69][CH2:70][N:65]([CH3:64])[CH2:66][CH:67]=4)=[CH:3][CH:4]=3)[N:9]=2)=[O:13])[CH2:22]1)=[O:33])([CH3:38])([CH3:37])[CH3:36]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 207733711-Methyl-1,2,3,6-tetrahydropyridine-4-boronic acid, pinacol esterHCID 86726911Benzyl {7-bromo-2-[({4-[(3S,5R)-3-[(tert-butoxycarbonyl)amino]-5-(trifluoromethyl)piperidin-1-yl]pyridin-3-yl}amino)carbonyl]quinolin-3-yl}carbamate

생성물 1

HCID 86726924
Benzyl [2-[({4-[(3S,5R)-3-[(tert-butoxycarbonyl)amino]-5-(trifluoromethyl)piperidin-1-yl]pyridin-3-yl}amino)carbonyl]-7-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)quinolin-3-yl]carbamate

시약·촉매·용매 2

HCID 178439015HCID 178439015, 화합물촉매HCID 962Water용매

반응 조건

온도
90 °C

실험 절차

A pressure vial was charged with benzyl {7-bromo-2-[({4-[(3S,5R)-3-[(tert-butoxycarbonyl)amino]-5-(trifluoromethyl)piperidin-1-yl]pyridin-3-yl}amino)carbonyl]quinolin-3-yl}carbamate (0.032 g, 0.043 mmol), K3PO4 (0.0181 g, 0.0852 mmol), 1,4-dioxane (0.55 mL), water (0.092 mL) and 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine (0.014 g, 0.063 mmol). The mixture was purged with nitrogen for 10 min. Dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine-(2′-aminobiphenyl-2-yl)(chloro)palladium (1:1) (0.0022 g, 0.0028 mmol) was added. The mixture was sealed with screw cap, then heated at 90° C. for 1.5 h. The mixture was quenched with water, then extracted with EtOAc. The combined organic layers were dried and concentrated under reduced pressure. The residue was purified by flash chromatography on 20 g silica gel, eluting with 0-30% MeOH in EtOAc, to yield the sub-title compound. LCMS calc. for C40H45F3N7O5 [M+H]+: m/z=760.3. found: 760.4.

후처리

  1. customThe mixture was purged with nitrogen for 10 min
  2. customThe mixture was sealed with screw
  3. customcap
  4. customThe mixture was quenched with water
  5. extractionextracted with EtOAc
  6. customThe combined organic layers were dried
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash chromatography on 20 g silica gel
  9. washeluting with 0-30% MeOH in EtOAc

출처 및 근거

ORD 기록
ord-a611fa7adc6d444092ebc518e2e051cc
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09278950B2

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