Dimethylformamide → HCID 69522294, compound

HRID 856579Notes

Reaction equation

HRID 856579 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]([OH:31])=O)=[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.[NH2:42][C:43]1[CH:62]=[CH:61][C:46]2[N:47]([CH3:60])[C:48]([S:50][CH2:51][C:52]3[N:56]([CH2:57][CH2:58][CH3:59])[CH:55]=[N:54][CH:53]=3)=[N:49][C:45]=2[CH:44]=1>O1CCCC1.N1C=CC=CC=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][CH:26]([CH3:27])[CH3:28])[CH2:23][CH2:22][C:21]([C:29]([NH:42][C:43]4[CH:62]=[CH:61][C:46]5[N:47]([CH3:60])[C:48]([S:50][CH2:51][C:52]6[N:56]([CH2:57][CH2:58][CH3:59])[CH:55]=[N:54][CH:53]=6)=[N:49][C:45]=5[CH:44]=4)=[O:31])=[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 22938658HCID 22938658, compound

Product 1

HCID 69522294HCID 69522294, compoundYield 66.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid (174 mg) in tetrahydrofuran (10 ml) was added one droplet of DMF. Then, thionyl chloride (0.038 ml) was added to the mixture, and the mixture was stirred for 1 hour under nitrogen atmosphere. This solution was slowly added dropwise to a solution of 5-amino-1-methyl-2-(((1-propylimidazol-5-yl)methyl)sulfanyl)benzimidazole (120 mg) in pyridine (10 ml) at 0° C. under nitrogen atmosphere. The mixture was stirred for 1 hour at room temperature under nitrogen atmosphere, water was added to the mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the obtained residue was purified by basic silica gel column chromatography (ethyl acetate), to give 7-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-N-[1-methyl-2-(((1-propylimidazol-5-yl)methyl)sulfanyl)benzimidazol-5-yl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide (191 mg) (Compound 444) as yellow amorphous.

Workup

  1. stirringThe mixture was stirred for 1 hour at room temperature under nitrogen atmosphere
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe obtained residue was purified by basic silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-5e41ce4ae5884ee1a53957ab13905381
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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