Dimethylformamide → HCID 69521907, compound

HRID 856505Notes

Reaction equation

HRID 856505 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]([CH3:28])[CH3:27])[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].CN(C=O)C.S(Cl)(Cl)=O.[N:42]1[CH:47]=[CH:46][CH:45]=[C:44]([CH2:48][S:49][C:50]2[CH:56]=[CH:55][C:53]([NH2:54])=[CH:52][CH:51]=2)[N:43]=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][CH:26]([CH3:27])[CH3:28])[CH2:23][CH2:22][C:21]([C:29]([NH:54][C:53]4[CH:55]=[CH:56][C:50]([S:49][CH2:48][C:44]5[N:43]=[N:42][CH:47]=[CH:46][CH:45]=5)=[CH:51][CH:52]=4)=[O:30])=[CH:20][C:19]=3[CH:32]=2)=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH3:4]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 223289057-[4-(2-Butoxyethoxy)phenyl]-1-isobutyl-2,3-dihydro-1-benzazepine-4-carboxylic acidHCID 69521807HCID 69521807, compound

Product 1

HCID 69521907HCID 69521907, compoundYield 13.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Procedure

7-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-2,3-dihydro-1-benzazepine-4-carboxylic acid (0.80 g) was dissolved in THF (16 ml), DMF (2 droplets) was added to the mixture, thionyl chloride (0.20 ml) was added to the mixture, and the solution was stirred at room temperature for 1 hour. The solution was added dropwise to a solution of 4-[(3-pyridazinylmethyl)sulfanyl]aniline (0.44 g) and triethylamine (2.55 ml) in THF (13.2 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 with silica gel column chromatography, to give 7-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-N-[4-[(3-pyridazinylmethyl)sulfanyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide (Compound 258) (0.16 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 with silica gel column chromatography

Sources & evidence

ORD record
ord-dcba192a247c4c46a1cd17bc7abfc315
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

Loading…