Dimethylformamide → HCID 178450536, compound

HRID 587072Notes

Reaction equation

HRID 587072 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][C:26]4[NH:30][N:29]=[N:28][N:27]=4)[CH2:23][CH2:22][C:21]([C:31]([OH:33])=O)=[CH:20][C:19]=3[CH:34]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4].[CH3:35][N:36]([CH:38]=O)[CH3:37].S(Cl)(Cl)=O.C([N:46]([CH2:49][CH3:50])CC)C.[CH2:51]1[CH2:55][O:54][CH2:53][CH2:52]1>O>[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][C:26]4[NH:30][N:29]=[N:28][N:27]=4)[CH2:23][CH2:22][C:21]([C:31]([NH:46][C:49]4[CH:50]=[CH:4][C:3]([CH2:38][N:36]([CH3:35])[CH:37]5[CH2:51][CH2:55][O:54][CH2:53][CH2:52]5)=[CH:2][CH:1]=4)=[O:33])=[CH:20][C:19]=3[CH:34]=2)=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 178450549HCID 178450549, compound

Product 1

HCID 178450536HCID 178450536, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In THF (8.1 ml) was dissolved 7-[4-(2-butoxyethoxy)phenyl]-1-(tetrazol-5-ylmethyl)-2,3-dihydro-1-benzazepine-4-carboxylic acid (0.27 g). To the solution was added DMF (two droplets), followed by addition of thionyl chloride (51 μl) and stirring at room temperature for 1 hour, to give a solution, which was added dropwise to a solution of 4-[methyl(tetrahydropyranyl-4-yl)aminomethyl]aniline (145 mg) and triethylamine (1.62 ml) in THF (8.1 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. The extract was washed with saturated brine and dried with magnesium sulfate. The solvent was removed under reduced pressure, and the resulting residue was dissolved in ethanol. To the solution was added ethyl acetate, and the precipitates were collected by filtration, which was recrystallized from hexane/ethanol to give 7-[4-(2-butoxyethoxy)phenyl]-N-[4-[N-methyl-N-(tetrahydropyran-4-yl)aminomethyl]phenyl]-1-(tetrazol-5-ylmethyl)-2,3-dihydro-1-benzazepine-4-carboxamide (Compound 100) (42 mg).

Workup

  1. customto give a solution, which
  2. temperaturecooling
  3. stirringthe mixture was stirred at room temperature for 2 hours
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried with magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. dissolutionthe resulting residue was dissolved in ethanol
  9. additionTo the solution was added ethyl acetate
  10. filtrationthe precipitates were collected by filtration, which
  11. customwas recrystallized from hexane/ethanol

Sources & evidence

ORD record
ord-1e6b43c9a5114b4893d8dea8ab5ae7fc
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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