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llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
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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
ノート
印刷プレビュー

反応式

HRID 924532 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 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

生成物 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}carbamate収率 66%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒
HCID 887
Methanol
溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-efb9cc6065bb415288fafb5a128b7b62
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09278950B2

反応ノート

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