Water → HCID 10283276, compound

HRID 856561Notes

Reaction equation

HRID 856561 reaction equation
[CH2:1]([N:5]1[C:11]2[CH:12]=[CH:13][C:14]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][CH3:28])=[CH:18][CH:17]=3)=[CH:15][C:10]=2[CH:9]=[C:8]([C:29]([NH:31][C:32]2[CH:37]=[CH:36][C:35]([S:38][CH2:39][C:40]3[N:44]([CH2:45][CH2:46][CH3:47])[CH:43]=[N:42][CH:41]=3)=[CH:34][CH:33]=2)=[O:30])[CH2:7][CH2:6]1)[CH:2]([CH3:4])[CH3:3].ClC1C=CC=C(C(OO)=[O:56])C=1.CSC.O>ClCCl>[CH2:1]([N:5]1[C:11]2[CH:12]=[CH:13][C:14]([C:16]3[CH:17]=[CH:18][C:19]([O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][CH3:28])=[CH:20][CH:21]=3)=[CH:15][C:10]=2[CH:9]=[C:8]([C:29]([NH:31][C:32]2[CH:37]=[CH:36][C:35]([S:38]([CH2:39][C:40]3[N:44]([CH2:45][CH2:46][CH3:47])[CH:43]=[N:42][CH:41]=3)=[O:56])=[CH:34][CH:33]=2)=[O:30])[CH2:7][CH2:6]1)[CH:2]([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 1068Dimethyl SulfideHCID 70297m-Chloroperbenzoic acidHCID 69522754HCID 69522754, compound

Product 1

HCID 10283276HCID 10283276, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-isobutyl-7-[4-(2-propoxyethoxy)phenyl]-N-[4-[[[1-propylimidazol-5-yl]methyl]sulfanyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide (600 mg) in dichloromethane (15 ml) was added dropwise 70% solution of 3-chloroperbenzoic acid (272 mg) in dichloromethane (15 ml) at −78° C. Dimethylsulfide (0.1 ml) was added to the mixture, and the mixture was allowed to be at room temperature and stirred for 30 minutes. To the mixture was added water and the mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous solution of saturated sodium bicarbonate, and saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure. The obtained residue was separated and purified by basic silica gel column chromatography (ethyl acetate), to give 1-isobutyl-7-[4-(2-propoxyethoxy)phenyl]-N-[4-[[[1-propylimidazol-5-yl]methyl]sulfinyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide (433 mg) (Compound 390) as yellow amorphous.

Workup

  1. customto be at room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with an aqueous solution of saturated sodium bicarbonate, and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe obtained residue was separated
  7. custompurified by basic silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-9d11b0d993664343af95929757c34096
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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