4-Methylmorpholine → 2-bromo-4,5-dimethoxy-N-[3-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-7-ylcarbamoyl)-benzyl]-benzamide

HRID 418356

Reaktionsgleichung

Reaktionsgleichung von HRID 418356
Cl.Cl.[CH3:3][N:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][C:8]([NH:14][C:15]([C:17]3[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=3)[CH2:20][NH2:21])=[O:16])=[CH:9][CH:10]=2)[CH2:5]1.CN1CCOCC1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Br:56][C:57]1[CH:65]=[C:64]([O:66][CH3:67])[C:63]([O:68][CH3:69])=[CH:62][C:58]=1[C:59](O)=[O:60]>CN(C=O)C>[Br:56][C:57]1[CH:65]=[C:64]([O:66][CH3:67])[C:63]([O:68][CH3:69])=[CH:62][C:58]=1[C:59]([NH:21][CH2:20][C:19]1[CH:22]=[CH:23][CH:24]=[C:17]([C:15](=[O:16])[NH:14][C:8]2[CH:7]=[C:6]3[C:11]([CH2:12][CH2:13][N:4]([CH3:3])[CH2:5]3)=[CH:10][CH:9]=2)[CH:18]=1)=[O:60]

Komponenten

6

Edukt 4

HCID 79724-MethylmorpholineHCID 2229632-Bromo-4,5-dimethoxybenzoic acid2×HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 666490723-(2-Methyl-1,2,3,4-tetrahydro-isoquinolin-7-ylcarbamoyl)benzylamine dihydrochloride

Produkt 1

HCID 591907692-bromo-4,5-dimethoxy-N-[3-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-7-ylcarbamoyl)-benzyl]-benzamideAusbeute 40,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

Dissolved 3-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-7-ylcarbamoyl)benzylamine dihydrochloride (36.8 mg, 0.10 mmol) in DMF (1.0 mL) and added 4-methylmorpholine (0.044 mL, 0.4 mmol). Dissolved HATU (57.0 mg, 0.15 mmol) in 1.0 mL DMF and added to the 2-bromo-4,5-dimethoxybenzoic acid (25.5 mg, 0.12 mmol) and stirred to dissolve. Added the amine to the 2-bromo-4,5-dimethoxybenzoic acid solution and shook at room temperature 48 hours. The solvent was removed under reduced pressure. The residue was dissolved in 10% water/DMSO (900 uL). Purified by prep HPLC to give 22.0 mg of 2-bromo-4,5-dimethoxy-N-[3-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-7-ylcarbamoyl)-benzyl]-benzamide. MS, electrospray, 538 (M+H).

Aufarbeitung

  1. dissolutionto dissolve
  2. stirringshook at room temperature 48 hours
  3. customThe solvent was removed under reduced pressure
  4. dissolutionThe residue was dissolved in 10% water/DMSO (900 uL)
  5. customPurified by prep HPLC

Quellen und Nachweise

ORD-Eintrag
ord-39593b923ea64bab88809329291ba2c0
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093266B2

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