Water → HCID 69522082, compound

HRID 856577Notes

Reaction equation

HRID 856577 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]([NH:31][C:32]4[CH:37]=[CH:36][C:35]([S:38][CH2:39][C:40]5[N:41]=[CH:42][N:43]([CH2:46][CH2:47][CH3:48])[C:44]=5[CH3:45])=[CH:34][CH:33]=4)=[O:30])=[CH:20][C:19]=3[CH:49]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4].ClC1C=CC=C(C(OO)=[O:58])C=1.CSC.O>ClCCl>[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:31][C:32]4[CH:33]=[CH:34][C:35]([S:38]([CH2:39][C:40]5[N:41]=[CH:42][N:43]([CH2:46][CH2:47][CH3:48])[C:44]=5[CH3:45])=[O:58])=[CH:36][CH:37]=4)=[O:30])=[CH:20][C:19]=3[CH:49]=2)=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 1068Dimethyl SulfideHCID 70297m-Chloroperbenzoic acidHCID 69521949HCID 69521949, compound

Product 1

HCID 69522082HCID 69522082, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 7-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-N-[4-[[(5-methyl-1-propylimidazol-4-yl)methyl]sulfanyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide (220 mg) in dichloromethane (10 ml) was added dropwise 70% solution of 3-chloroperbenzoic acid (119 mg) in dichloromethane (10 ml) at −78° C., and the mixture was stirred for 30 minutes at the same temperature. 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: and the obtained residue was separated and purified by basic silica gel column chromatography (ethyl acetate→ethyl acetate:methanol=10:1), to give 7-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-N-[4-[[(5-methyl-1-propylimidazol-4-yl)methyl]sulfinyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide (132 mg) (Compound 441) as yellow amorphous.

Workup

  1. customto be at room temperature
  2. stirringstirred for 30 minutes
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with an aqueous solution of saturated sodium bicarbonate, and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe obtained residue was separated
  8. custompurified by basic silica gel column chromatography (ethyl acetate→ethyl acetate:methanol=10:1)

Sources & evidence

ORD record
ord-5368c727514a40cd8f756e00253057a2
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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