Dimethylformamide → 7-[4-(2-butoxyethoxy)phenyl]-1-[(1-methylpyrazol-4-yl)methyl]-N-[4-[[methyl(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide

HRID 586968Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 586968
CN(C=O)C.[CH2:6]([O:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:21]=[CH:22][C:23]3[N:29]([CH2:30][C:31]4[CH:32]=[N:33][N:34]([CH3:36])[CH:35]=4)[CH2:28][CH2:27][C:26]([C:37](O)=[O:38])=[CH:25][C:24]=3[CH:40]=2)=[CH:16][CH:15]=1)[CH2:7][CH2:8][CH3:9].S(Cl)(Cl)=O.[CH3:45][N:46]([CH2:53][C:54]1[CH:60]=[CH:59][C:57]([NH2:58])=[CH:56][CH:55]=1)[CH:47]1[CH2:52][CH2:51][O:50][CH2:49][CH2:48]1>ClCCl.O.C(N(CC)CC)C>[CH2:6]([O:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:21]=[CH:22][C:23]3[N:29]([CH2:30][C:31]4[CH:32]=[N:33][N:34]([CH3:36])[CH:35]=4)[CH2:28][CH2:27][C:26]([C:37]([NH:58][C:57]4[CH:59]=[CH:60][C:54]([CH2:53][N:46]([CH3:45])[CH:47]5[CH2:52][CH2:51][O:50][CH2:49][CH2:48]5)=[CH:55][CH:56]=4)=[O:38])=[CH:25][C:24]=3[CH:40]=2)=[CH:16][CH:15]=1)[CH2:7][CH2:8][CH3:9]

Komponenten

8

Edukt 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 9877845(4-Amino-benzyl)-methyl-(tetrahydro-pyran-4-yl)-amineHCID 69746837HCID 69746837, Verbindung

Produkt 1

HCID 30094197-[4-(2-butoxyethoxy)phenyl]-1-[(1-methylpyrazol-4-yl)methyl]-N-[4-[[methyl(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamideAusbeute 62,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

One droplet of DMF was added to a solution of 7-(4-butoxyethoxyphenyl)-1-[(1-methypyrazol-4-yl)methyl]-2,3-dihydro-1-benzazepine-4-carboxylic acid (380 mg) in dichloromethane (20 ml). Then, thionyl chloride (124 mg) was added at 0° C., the temperature was returned to room temperature, and the mixture was stirred under nitrogen atmosphere for 1 hour. Then, this solution was added to a solution of 4-[[N-methyl N-(tetrahydropyran-4-yl)amino]methyl]aniline (229 mg) and triethylamine (2.1 g) in dichloromethane (30 ml) at 0° C. The suspension was stirred under nitrogen atmosphere at room temperature overnight, to the mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried with magnesium sulfate. The solvent was evaporated under reduced pressure, the resulting residue was separated and purified with silica gel column chromatography (methanol:ethyl acetate=1:3), which was recrystallized from hexane-ethyl acetate to give 7-(4-butoxyethoxyphenyl)-1-[(1-methylpyrazol-4-yl)methyl]-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide (Compound 69) (338 mg) as yellow crystals.

Aufarbeitung

  1. customwas returned to room temperature
  2. stirringThe suspension was stirred under nitrogen atmosphere at room temperature overnight, to the mixture
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried with magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe resulting residue was separated
  8. custompurified with silica gel column chromatography (methanol:ethyl acetate=1:3), which
  9. customwas recrystallized from hexane-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-85bda59c5417401a9c959932b3107d6b
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06936602B1

Notizen zur Reaktion

Wird geladen…