Morpholine → 1-((2S,4R)-2-methyl-6-(4-(morpholine-4-carbonyl)phenyl)-4-(pyridin-2-ylamino)-3,4-dihydroquinolin-1(2H)-yl)ethanone formate

HRID 882296노트

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HRID 882296 반응식
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([O-:20])=[O:19])=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)[CH2:6][C@@H:5]1[CH3:30])(=[O:3])[CH3:2].[Li+].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH:65]1[CH2:70][CH2:69][O:68][CH2:67][CH2:66]1>CN(C=O)C.O>[CH:18]([OH:20])=[O:19].[CH3:30][C@H:5]1[CH2:6][C@@H:7]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)[C:8]2[C:13](=[CH:12][CH:11]=[C:10]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([N:65]4[CH2:70][CH2:69][O:68][CH2:67][CH2:66]4)=[O:20])=[CH:16][CH:15]=3)[CH:9]=2)[N:4]1[C:1](=[O:3])[CH3:2]

참가 물질

7

반응물 4

HCID 8083Morpholine2회HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 70976493lithium 4-((2S,4R)-1-acetyl-2-methyl-4-(pyridin-2-ylamino)-1,2,3,4-tetrahydroquinolin-6-yl)benzoate

생성물 1

HCID 714686411-((2S,4R)-2-methyl-6-(4-(morpholine-4-carbonyl)phenyl)-4-(pyridin-2-ylamino)-3,4-dihydroquinolin-1(2H)-yl)ethanone formate수율 10%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

Crude lithium 4-((2S,4R)-1-acetyl-2-methyl-4-(pyridin-2-ylamino)-1,2,3,4-tetrahydroquinolin-6-yl)benzoate (for a preparation see Intermediate 58) (40 mg) and HATU (41 mg, 0.108 mmol) in DMF (0.5 mL) were treated with DIPEA (51.2 μL, 0.294 mmol) and the mixture shaken and sonicated until a solution was formed (<2 min). This solution was added to morpholine (17 μL, 0.194 mmol), the mixture briefly shaken then left to stand at room temperature for 2 h. A further portion of morpholine (34 μL, 0.388 mmol) was added and the mixture left to stand overnight. The mixture was diluted with water and extracted three times with DCM. The combined organic layers were dried by passing through a hydrophobic frit and concentrated in vacuo to give a residue. The residue was purified by MDAP (formate) to give 1-((2S,4R)-2-methyl-6-(4-(morpholine-4-carbonyl)phenyl)-4-(pyridin-2-ylamino)-3,4-dihydroquinolin-1(2H)-yl)ethanone formate (20 mg, 0.039 mmol, 10% yield) as a pale pink glass.

후처리

  1. customsonicated until a solution
  2. customwas formed (<2 min)
  3. stirringthe mixture briefly shaken
  4. waitthen left
  5. waitthe mixture left
  6. waitto stand overnight
  7. extractionextracted three times with DCM
  8. customThe combined organic layers were dried
  9. concentrationconcentrated in vacuo
  10. customto give a residue
  11. customThe residue was purified by MDAP (formate)

출처 및 근거

ORD 기록
ord-90035d076a324f2391d1fdf911a6a2e2
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08993554B2

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