Dimethylformamide → 7-[4-(2-butoxyethoxy)phenyl]-1-propyl-N-[6-[(3-pyridinylmethyl)sulfanyl]-3-pyridinyl]-2,3-dihydro-1-benzazepine-4-carboxamide

HRID 856513Notes

Reaction equation

HRID 856513 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][CH2:26][CH3:27])[CH2:23][CH2:22][C:21]([C:28](O)=[O:29])=[CH:20][C:19]=3[CH:31]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4].CN(C=O)C.S(Cl)(Cl)=O.[N:41]1[CH:46]=[CH:45][CH:44]=[C:43]([CH2:47][S:48][C:49]2[N:54]=[CH:53][C:52]([NH2:55])=[CH:51][CH:50]=2)[CH:42]=1>C1COCC1.O.C(N(CC)CC)C>[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][CH2:26][CH3:27])[CH2:23][CH2:22][C:21]([C:28]([NH:55][C:52]4[CH:53]=[N:54][C:49]([S:48][CH2:47][C:43]5[CH:42]=[N:41][CH:46]=[CH:45][CH:44]=5)=[CH:50][CH:51]=4)=[O:29])=[CH:20][C:19]=3[CH:31]=2)=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH3:4]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 114301667-[4-(2-Butoxyethoxy)phenyl]-1-propyl-2,3-dihydro-1-benzazepine-4-carboxylic acidHCID 433014866-[(3-Pyridinylmethyl)sulfanyl]-3-pyridinylamine

Product 1

HCID 695212047-[4-(2-butoxyethoxy)phenyl]-1-propyl-N-[6-[(3-pyridinylmethyl)sulfanyl]-3-pyridinyl]-2,3-dihydro-1-benzazepine-4-carboxamideYield 25%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Procedure

In THF (50 ml) was dissolved 7-[4-(2-butoxyethoxy)phenyl]-1-propyl-2,3-dihydro-1-benzazepine-4-carboxylic acid (2.5 g), and DMF (5 droplets) was added to the mixture, thionyl chloride (0.86 ml) was added to the mixture, and the mixture was stirred at room temperature for 1 hour. The solution was added dropwise to a solution of 6-[(3-pyridinylmethyl)sulfanyl]-3-pyridinylamine (1.41 g) and triethylamine (12.3 ml) in THF (42.3 ml) under ice-cooling, and the mixture was stirred for 2 hours at room temperature. The reaction solution was added to water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography, to give 7-[4-(2-butoxyethoxy)phenyl]-1-propyl-N-[6-[(3-pyridinylmethyl)sulfanyl]-3-pyridinyl]-2,3-dihydro-1-benzazepine-4-carboxamide (Compound 273) (0.92 g).

Workup

  1. additionwas added to the mixture
  2. temperaturecooling
  3. stirringthe mixture was stirred for 2 hours at room temperature
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-430dde1f766745b19b7f2bb4d8a963ee
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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