Dimethylformamide → 7-[4-(2-Butoxyethoxy)phenyl]-1-crotyl-n-[4-[n-methyl-n-(tetrahydropyran-4-yl)aminomethyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide

HRID 587036Notes

Reaction equation

HRID 587036 reaction equation
[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:24]([CH2:25][CH:26]=[CH:27][CH3:28])[CH2:23][CH2:22][C:21]([C:29](O)=[O:30])=[CH:20][C:19]=3[CH:32]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4].S(Cl)(Cl)=O.[CH3:37][N:38]([CH:40]=O)[CH3:39]>>[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:24]([CH2:25][CH:26]=[CH:27][CH3:28])[CH2:23][CH2:22][C:21]([C:29]([NH:24][C:18]4[CH:19]=[CH:32][C:15]([CH2:40][N:38]([CH3:37])[CH:39]5[CH2:7][CH2:6][O:5][CH2:1][CH2:2]5)=[CH:16][CH:17]=4)=[O:30])=[CH:20][C:19]=3[CH:32]=2)=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 69747294HCID 69747294, compound

Product 1

HCID 697471097-[4-(2-Butoxyethoxy)phenyl]-1-crotyl-n-[4-[n-methyl-n-(tetrahydropyran-4-yl)aminomethyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide

Procedure

In DMF (3.9 ml) was dissolved 7-[4-(2-butoxyethoxy)phenyl)-1-crotyl-2,3-dihydro-1-benzazepine-4-carboxylic acid (0.20 g). To the solution was added thionyl chloride (82 μl), and the mixture was stirred at room temperature for 1 hour. The solvent was removed under reduced pressure, and a solution of the resulting residue in THF was added dropwise to a solution of 4-[methyl(tetrahydropyranyl-4-yl)aminomethyl]aniline (111 mg) and triethylamine (0.31 ml) in THF (3.3 ml) under ice-cooling, and the mixture was stirred at room temperature for 2 hours. The reaction solution was added to water, and the mixture was extracted with ethyl acetate, washed with saturated brine and dried with magnesium sulfate. The solvent was removed under reduced pressure, and the resulting residue was purified with silica gel column chromatography (ethyl acetate/ethanol=4/1), which was recrystallized from isopropyl ether/ethyl acetate to give 7-[4-(2-butoxyethoxy)phenyl]-1-crotyl-N-[4-[N-methyl-N-(tetrahydropyran-4-yl)aminomethyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide (Compound 83) (9 mg).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additiona solution of the resulting residue in THF was added dropwise to a solution of 4-[methyl(tetrahydropyranyl-4-yl)aminomethyl]aniline (111 mg) and triethylamine (0.31 ml) in THF (3.3 ml) under ice-
  3. temperaturecooling
  4. stirringthe mixture was stirred at room temperature for 2 hours
  5. additionThe reaction solution was added to water
  6. extractionthe mixture was extracted with ethyl acetate
  7. washwashed with saturated brine
  8. dry with materialdried with magnesium sulfate
  9. customThe solvent was removed under reduced pressure
  10. customthe resulting residue was purified with silica gel column chromatography (ethyl acetate/ethanol=4/1), which
  11. customwas recrystallized from isopropyl ether/ethyl acetate

Sources & evidence

ORD record
ord-c1239688fad947a8abe665dc1ea4a2db
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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