tert-Butyl methyl [(3R,4S,5S)-1-(3-{[(3-{[(benzyloxy)carbonyl]amino}-7-vinylquinolin-2-yl)carbonyl]amino}pyridin-4-yl)-5-methylpiperidine-3, 4-diyl]biscarbamate → Methyl [(3R,4S,5S)-3-amino-1-(3-{[(3-amino-7-ethylquinolin-2-yl)carbonyl]amino}pyridin-4-yl)-5-methylpiperidin-4-yl]carbamate

HRID 924524노트

반응식

HRID 924524 반응식
C(OC([NH:11][C:12]1[C:13]([C:24]([NH:26][C:27]2[CH:28]=[N:29][CH:30]=[CH:31][C:32]=2[N:33]2[CH2:38][C@H:37]([CH3:39])[C@H:36]([NH:40][C:41](=[O:44])[O:42][CH3:43])[C@H:35]([NH:45]C(=O)OC(C)(C)C)[CH2:34]2)=[O:25])=[N:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[C:17]([CH:22]=[CH2:23])[CH:16]=2)=O)C1C=CC=CC=1>CO.[Pd]>[NH2:45][C@H:35]1[C@@H:36]([NH:40][C:41](=[O:44])[O:42][CH3:43])[C@@H:37]([CH3:39])[CH2:38][N:33]([C:32]2[CH:31]=[CH:30][N:29]=[CH:28][C:27]=2[NH:26][C:24]([C:13]2[C:12]([NH2:11])=[CH:21][C:20]3[C:15](=[CH:16][C:17]([CH2:22][CH3:23])=[CH:18][CH:19]=3)[N:14]=2)=[O:25])[CH2:34]1

참가 물질

4

반응물 1

HCID 86726963tert-Butyl methyl [(3R,4S,5S)-1-(3-{[(3-{[(benzyloxy)carbonyl]amino}-7-vinylquinolin-2-yl)carbonyl]amino}pyridin-4-yl)-5-methylpiperidine-3, 4-diyl]biscarbamate

생성물 1

HCID 90287259Methyl [(3R,4S,5S)-3-amino-1-(3-{[(3-amino-7-ethylquinolin-2-yl)carbonyl]amino}pyridin-4-yl)-5-methylpiperidin-4-yl]carbamate수율 73%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

To a solution of tert-butyl methyl [(3R,4S,5S)-1-(3-{[(3-{[(benzyloxy)carbonyl]amino}-7-vinylquinolin-2-yl)carbonyl]amino}pyridin-4-yl)-5-methylpiperidine-3,4-diyl]biscarbamate (92 mg, 0.13 mmol) in MeOH (4.0 mL), 10% Pd on carbon (21 mg) was added. 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 1 h. The mixture was then filtered and concentrated under reduced pressure. The resulting residue was dissolved in DCM (2 mL), and TFA (2 mL) was added. The mixture then was stirred at room temperature for 1 h before being 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 (45 mg, 73%). LCMS calc. for C25H32N7O3 (M+H)+: m/z=478.3. Found: 478.3.

후처리

  1. customThe reaction mixture was deoxygenated under reduced pressure and hydrogen
  2. additionwas introduced via a balloon
  3. filtrationThe mixture was then 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 then was stirred at room temperature for 1 h
  8. concentrationbefore being 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-4b444c0137c54e4a9fac9e0cc7857ad5
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278950B2

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