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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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tert-Butyl methyl {(3R,4S,5S)-1-[3-({[3-{[(benzyloxy)carbonyl]amino}-7-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)quinolin-2-yl]carbonyl}amino)pyridin-4-yl]-5-methylpiperidine-3, 4-diyl}biscarbamate → Methyl {(3R,4S,5S)-3-amino-1-[3-({[3-amino-7-(1-methylpiperidin-4-yl)quinolin-2-yl]carbonyl}amino)pyridin-4-yl]-5-methylpiperidin-4-yl}carbamate

HRID 924532
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HRID 924532 반응식
C(OC([NH:11][C:12]1[C:13]([C:29]([NH:31][C:32]2[CH:33]=[N:34][CH:35]=[CH:36][C:37]=2[N:38]2[CH2:43][C@H:42]([CH3:44])[C@H:41]([NH:45][C:46](=[O:49])[O:47][CH3:48])[C@H:40]([NH:50]C(=O)OC(C)(C)C)[CH2:39]2)=[O:30])=[N:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[C:17]([C:22]1[CH2:23][CH2:24][N:25]([CH3:28])[CH2:26][CH:27]=1)[CH:16]=2)=O)C1C=CC=CC=1>CO.[Pd]>[NH2:50][C@H:40]1[C@@H:41]([NH:45][C:46](=[O:49])[O:47][CH3:48])[C@@H:42]([CH3:44])[CH2:43][N:38]([C:37]2[CH:36]=[CH:35][N:34]=[CH:33][C:32]=2[NH:31][C:29]([C:13]2[C:12]([NH2:11])=[CH:21][C:20]3[C:15](=[CH:16][C:17]([CH:22]4[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]4)=[CH:18][CH:19]=3)[N:14]=2)=[O:30])[CH2:39]1
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참가 물질

4

반응물 1

HCID 86726970tert-Butyl methyl {(3R,4S,5S)-1-[3-({[3-{[(benzyloxy)carbonyl]amino}-7-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)quinolin-2-yl]carbonyl}amino)pyridin-4-yl]-5-methylpiperidine-3, 4-diyl}biscarbamate

생성물 1

HCID 86726971Methyl {(3R,4S,5S)-3-amino-1-[3-({[3-amino-7-(1-methylpiperidin-4-yl)quinolin-2-yl]carbonyl}amino)pyridin-4-yl]-5-methylpiperidin-4-yl}carbamate수율 66%

시약·촉매·용매 2

HCID 23938Palladium촉매
HCID 887
Methanol
용매

실험 절차

To a solution of tert-butyl methyl {(3R,4S,5S)-1-[3-({[3-{[(benzyloxy)carbonyl]amino}-7-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)quinolin-2-yl]carbonyl}amino)pyridin-4-yl]-5-methylpiperidine-3,4-diyl}biscarbamate (40 mg, 0.051 mmol) in MeOH (3.0 mL), 10% Pd on carbon (9 mg). The reaction mixture was deoxygenated under reduced pressure and hydrogen was introduced via a balloon. The reaction mixture was stirred at room temperature under hydrogen for 16 h. The mixture was filtered and concentrated under reduced pressure. The resulting residue was dissolved in DCM (2 mL), and TFA (2 mL) was added. The mixture was stirred at room temperature for 30 min. then concentrated under reduced pressure. The residue was purified by preparative LCMS (pH=10 method; XBridge™ preparative C18 5 μm OBD™ column, 30×10 mm, 60 mL/min., eluting with a gradient of MeCN and water with 0.1% NH4OH) to give the title compound as a yellow powder (18 mg, 66%). LCMS calc. for C29H39N8O3 (M+H)+: m/z=547.3. Found: 547.4.

후처리

  1. customThe reaction mixture was deoxygenated under reduced pressure and hydrogen
  2. additionwas introduced via a balloon
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe resulting residue was dissolved in DCM (2 mL)
  6. additionTFA (2 mL) was added
  7. stirringThe mixture was stirred at room temperature for 30 min.
  8. concentrationthen concentrated under reduced pressure
  9. customThe residue was purified by preparative LCMS (pH=10 method
  10. washXBridge™ preparative C18 5 μm OBD™ column, 30×10 mm, 60 mL/min., eluting with a gradient of MeCN and water with 0.1% NH4OH)

출처 및 근거

ORD 기록
ord-efb9cc6065bb415288fafb5a128b7b62
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09278950B2

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