Dichloromethane → tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(4-methyl-7-((methylamino) carbonyl)-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate

HRID 2193202Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2193202
ClCCl.[C:4]([O:8][C:9]([N:11]([CH2:35][C:36]1[CH:45]=[CH:44][C:39]2[O:40][CH2:41][CH2:42][O:43][C:38]=2[CH:37]=1)[CH:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][N:20]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([C:30]([OH:32])=O)[CH:28]=3)[C:23]([CH3:33])=[CH:22][C:21]2=[O:34])[CH2:14][CH2:13]1)=[O:10])([CH3:7])([CH3:6])[CH3:5].Cl.CN.F[P-](F)(F)(F)(F)F.[N:56]1(OC(N(C)C)=[N+](C)C)[C:60]2N=CC=CC=2N=N1>C(OCC)(=O)C.O.C(N(CC)CC)C>[C:4]([O:8][C:9](=[O:10])[N:11]([CH2:35][C:36]1[CH:45]=[CH:44][C:39]2[O:40][CH2:41][CH2:42][O:43][C:38]=2[CH:37]=1)[CH:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][N:20]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([C:30]([NH:56][CH3:60])=[O:32])[CH:28]=3)[C:23]([CH3:33])=[CH:22][C:21]2=[O:34])[CH2:14][CH2:13]1)([CH3:5])([CH3:6])[CH3:7]

Komponenten

8

Edukt 4

HCID 6344DichloromethaneHCID 6364545Methylamine hydrochloride2×HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)2×HCID 59397939HCID 59397939, Verbindung

Produkt 1

HCID 59398071tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(4-methyl-7-((methylamino) carbonyl)-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamateAusbeute 56,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8471TriethylamineLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To 1.7 mL of dichloromethane solution containing 0.10 g of 1-(2-(4-((tert-butoxycarbonyl)(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-4-methyl-2-oxo-1,2-dihydroquinoline-7-carboxylic acid, 13 mg of methylamine hydrochloride, 0.12 g of O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate and 89 μL of triethylamine were added at room temperature, stirred for 30 min, and allowed to stand for 12 hours. Further, 13 mg of methylamine hydrochloride, 0.12 g of O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate, and 89 μL of triethylamine were added. Water and ethyl acetate were added, the insoluble material was filtered off, the organic layer was separated, washed with aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by basic silica gel column chromatography [eluent; chloroform:water=100:1], to give 58 mg of tert-butyl(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(4-methyl-7-((methylamino)carbonyl)-2-oxo-1,2-dihydroquinolin-1-yl)ethyl)piperidin-4-yl)carbamate as a brown oil.

Aufarbeitung

  1. additionwere added at room temperature
  2. waitto stand for 12 hours
  3. filtrationthe insoluble material was filtered off
  4. customthe organic layer was separated
  5. washwashed with aqueous saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by basic silica gel column chromatography [eluent; chloroform:water=100:1]

Quellen und Nachweise

ORD-Eintrag
ord-1dc74e82b8f749ab926f9546e5dac051
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08329694B2

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