Dimethylformamide → HCID 22329206, compound

HRID 587095Notes

Reaction equation

HRID 587095 reaction equation
[CH3:1][N:2]([CH:4]=O)[CH3:3].[CH3:6][O:7][C:8]1[CH:38]=[CH:37][CH:36]=[CH:35][C:9]=1[CH2:10][N:11]1[C:17]2[CH:18]=[CH:19][C:20]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][CH3:31])=[CH:24][CH:23]=3)=[CH:21][C:16]=2[CH:15]=[C:14]([C:32]([OH:34])=O)[CH2:13][CH2:12]1.S(Cl)(Cl)=O>O1CCCC1>[CH3:6][O:7][C:8]1[CH:38]=[CH:37][CH:36]=[CH:35][C:9]=1[CH2:10][N:11]1[C:17]2[CH:18]=[CH:19][C:20]([C:22]3[CH:23]=[CH:24][C:25]([O:28][CH2:29][CH2:30][CH3:31])=[CH:26][CH:27]=3)=[CH:21][C:16]=2[CH:15]=[C:14]([C:32]([NH:11][C:17]2[CH:18]=[CH:19][C:20]([CH2:4][N:2]([CH3:1])[CH:3]3[CH2:30][CH2:29][O:28][CH2:25][CH2:24]3)=[CH:21][CH:16]=2)=[O:34])[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 22329081HCID 22329081, compound

Product 1

HCID 22329206HCID 22329206, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

One droplet of DMF was added to a solution of 1-(2-methoxybenzyl)-7-(4-propoxyphenyl)-2,3-dihydro-1-benzazepine-4-carboxylic acid (340 mg) in tetrahydrofuran (10 ml). Then, thionyl chloride (267 mg) was added thereto at 0° C., the temperature was returned to room temperature, and the mixture was stirred for 1 hour under nitrogen atmosphere. The solvent and excess thionyl chloride were evaporated under reduced pressure, and the resulting residue was suspended in tetrahydrofuran (30 ml), which was added to a solution of 4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]aniline (197 mg) and triethylamine (906 mg) in tetrahydrofuran (10 ml) at 0° C. The mixture was stirred at room temperature for 1 hour under nitrogen atmosphere, water was added thereto, 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=1:8), which was recrystallized from hexane-ethyl acetate to give 1-(2-methoxybenzyl)-N-[4-[[N-methyl N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-7-(4-propoxyphenyl)-2,3-dihydro-1-benzazepine-4-carboxamide (337 mg) as yellow crystals.

Workup

  1. customat 0° C.
  2. customwas returned to room temperature
  3. customThe solvent and excess thionyl chloride were evaporated under reduced pressure
  4. additionwhich was added to a solution of 4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]aniline (197 mg) and triethylamine (906 mg) in tetrahydrofuran (10 ml) at 0° C
  5. stirringThe mixture was stirred at room temperature for 1 hour under nitrogen atmosphere
  6. additionwater was added
  7. extractionthe mixture was extracted with ethyl acetate
  8. washThe organic layer was washed with saturated brine
  9. dry with materialdried with magnesium sulfate
  10. customThe solvent was evaporated under reduced pressure
  11. customthe resulting residue was separated
  12. custompurified with silica gel column chromatography (methanol:ethyl acetate=1:8), which
  13. customwas recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-4d4ba36c75904408b069a48dbcc70a44
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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