Ethylamine hydrochloride → (2S)-N-{[4-(3,4-dichlorobenzyl)morpholin-2-yl]methyl}-[4-(ethylaminocarbonyl)thiazol-2-ylthio]acetamide hydrochloride

HRID 545110Notes

Reaction equation

HRID 545110 reaction equation
[C:1]([C:4]1[N:5]=[C:6]([S:9][CH2:10][C:11]([NH:13][CH2:14][C@@H:15]2[O:20][CH2:19][CH2:18][N:17]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=3)[CH2:16]2)=[O:12])[S:7][CH:8]=1)(O)=[O:2].Cl.[CH2:31]([NH2:33])[CH3:32].Cl.CN(C)CCCN=C=NCC.O.OC1C2N=NNC=2C=CC=1.C(=O)([O-])O.[Na+]>CN(C)C=O.C(N(CC)CC)C>[ClH:28].[Cl:29][C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][C:25]=1[Cl:28])[CH2:21][N:17]1[CH2:18][CH2:19][O:20][C@@H:15]([CH2:14][NH:13][C:11](=[O:12])[CH2:10][S:9][C:6]2[S:7][CH:8]=[C:4]([C:1]([NH:33][CH2:31][CH3:32])=[O:2])[N:5]=2)[CH2:16]1

Participants

8

Reactant 5

HCID 11198Ethylamine hydrochlorideHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59009100(2S)-(4-carboxythiazol-2-ylthio)-N-{[4-(3,4-dichlorobenzyl)morpholin-2-yl]methyl}acetamideHCID 178526939HCID 178526939, compound

Product 1

HCID 67170019(2S)-N-{[4-(3,4-dichlorobenzyl)morpholin-2-yl]methyl}-[4-(ethylaminocarbonyl)thiazol-2-ylthio]acetamide hydrochloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

The resultant product (476 mg) of (1-5) and ethylamine hydrochloride (98 mg) were dissolved in dimethylformamide (2 mL), then 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (288 mg), hydroxybenzotriazole hydrate (230 mg) and triethylamine (167 μL) were added, and the mixture was stirred overnight at room temperature. A saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography using a mixed solvent of chloroform and methanol as an eluent. The solvent was evaporated from the eluent to give the title compound (free form, 441 mg) as a pale-yellow amorphous solid. By a similar method as in (1-2), the title compound (357 mg) was obtained as pale-yellow crystals from the obtained residue.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography
  6. customThe solvent was evaporated from the eluent

Sources & evidence

ORD record
ord-d6b57fee7efb4697a60c1d27d4771daf
Source dataset
uspto-grants-2011_05
Patent number
US07935700B2

Reaction notes

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