Dimethylformamide → HCID 69521870, compound

HRID 587079Notes

Reaction equation

HRID 587079 reaction equation
C(OCCOC1C=CC([C:15]2[CH:16]=[CH:17][C:18]3[N:24](CC4(C)OCCO4)[CH2:23][CH2:22][C:21]([C:32](O)=[O:33])=[CH:20][C:19]=3[CH:35]=2)=CC=1)CCC.S(Cl)(Cl)=O.C[N:41](C=O)C.CN(CC1C=CC(N)=CC=1)C1CCOCC1>C1COCC1.O.C(N(CC)CC)C>[NH:24]1[C:18]2[CH:17]=[CH:16][CH:15]=[CH:35][C:19]=2[CH:20]=[C:21]([C:32]([NH2:41])=[O:33])[CH2:22][CH2:23]1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 9877845(4-Amino-benzyl)-methyl-(tetrahydro-pyran-4-yl)-amineHCID 22329049HCID 22329049, compound

Product 1

HCID 69521870HCID 69521870, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a solution of 7-[4-(2-butoxyethoxy)phenyl]-1-[(2-methyl-1,3-dioxolan-2-yl)methyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid (300 mg) in THF (10 ml) were added thionyl chloride (0.068 ml) and DMF (one droplet) at room temperature, and the mixture was stirred for 1 hour. The reaction mixture was added dropwise to a solution of 4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]aniline (151 mg) and triethylamine (0.7 ml) in THF (3 ml) at 0° C. The mixture was stirred at room temperature for 20 hours, 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. After concentration under reduced pressure, the residue was separated and purified with column chromatography (ethanol:ethyl acetate=1:19→1:10), and the resulting crystals were purified by recrystallization (ethyl acetate-diisopropyl ether) to give 7-[4-(2-butoxyethoxy)phenyl]-1-[(2-methyl-1,3-dioxolan-2-yl)methyl]-N-[4-[[N-methyl-N-tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide (Compound 107) (144 mg) as yellow crystals.

Workup

  1. stirringThe mixture was stirred at room temperature for 20 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried with magnesium sulfate
  5. concentrationAfter concentration under reduced pressure
  6. customthe residue was separated
  7. custompurified with column chromatography (ethanol:ethyl acetate=1:19→1:10)
  8. customthe resulting crystals were purified by recrystallization (ethyl acetate-diisopropyl ether)

Sources & evidence

ORD record
ord-28bea5950ec344b8b6ca310c77f941e4
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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