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

HRID 586972Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 586972
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:36]=[CH:35][CH:34]=[CH:33][N:32]=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:15]=[CH:16][C:17]([C:20]2[CH:21]=[CH:22][C:23]3[N:29]([CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=4)[CH2:28][CH2:27][C:26]([C:37]([NH:58][C:57]4[CH:56]=[CH:55][C:54]([CH2:53][N:46]([CH3:45])[CH:47]5[CH2:52][CH2:51][O:50][CH2:49][CH2:48]5)=[CH:60][CH:59]=4)=[O:38])=[CH:25][C:24]=3[CH:40]=2)=[CH:18][CH:19]=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 69747253HCID 69747253, Verbindung

Produkt 1

HCID 223293307-(4-butoxyethoxyphenyl)-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-1-(2-pyridylmethyl)-2,3-dihydro-1-benzazepine-4-carboxamideAusbeute 43,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

One droplet of DMF was added to a solution of 7-(4-butoxyethoxyphenyl)-1-(2-pyridylmethyl)-2,3-dihydro-1-benzazepine-4-carboxylic acid (50 mg) in dichloromethane (5 ml). Then, thionyl chloride (17 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 (31 mg) and triethylamine (287 mg) in dichloromethane (15 ml) at 0° C. The mixture 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, and the resulting residue was separated and purified with silica gel column chromatography (methanol:ethyl acetate=1:3) to give 7-(4-butoxyethoxyphenyl)-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-1-(2-pyridylmethyl)-2,3-dihydro-1-benzazepine-4-carboxamide (Compound 73) (31 mg) as yellow amorphous.

Aufarbeitung

  1. customwas returned to room temperature
  2. stirringThe mixture 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)

Quellen und Nachweise

ORD-Eintrag
ord-8240bea749504cfc8cc6ac6dcc8e6179
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06936602B1

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