Dimethylformamide → HCID 69522671, compound

HRID 856529Notes

Reaction equation

HRID 856529 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.[S:42]1[CH:46]=[CH:45][N:44]=[C:43]1[CH2:47][S:48][C:49]1[CH:55]=[CH:54][C:52]([NH2:53])=[CH:51][CH:50]=1>O1CCCC1.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]([CH3:28])[CH3:27])[CH2:23][CH2:22][C:21]([C:29]([NH:53][C:52]4[CH:54]=[CH:55][C:49]([S:48][CH2:47][C:43]5[S:42][CH:46]=[CH:45][N:44]=5)=[CH:50][CH:51]=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 69521922HCID 69521922, compound

Product 1

HCID 69522671HCID 69522671, compoundYield 66%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a solution of 7-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-2,3-dihydro-1-benzazepine-4-carboxylic acid (438 mg) in tetrahydrofuran (10 ml) was added one droplet of DMF. Then, thionyl chloride (0.095 ml) was added to the mixture at 0° C., and the mixture was allowed to be at room temperature under nitrogen atmosphere and the mixture was stirred for 1 hour. This solution was added to a solution of 4-[(thiazol-2-ylmethyl)sulfanyl]aniline (265 mg) and triethylamine (3.6 ml) in tetrahydrofuran (10 ml) at 0° C. The mixture was stirred overnight 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 saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) and was recrystallized from hexane-ethyl acetate, to give 7-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-N-[4-[(thiazol-2-ylmethyl)sulfanyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide (424 mg) (Compound 316) as yellow crystals.

Workup

  1. customto be at room temperature under nitrogen atmosphere
  2. stirringThe mixture was stirred overnight at room temperature under nitrogen atmosphere
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)
  8. customwas recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-6b7489bd34db479eaec36ae8cad78054
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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