Triethylamine → tert-Butyl 3-[4-{[(4-chlorobenzyl)(methyl)amino]methyl}-2-{[4-(trifluoromethoxy)phenyl]imino}thiazol-3(2H)-yl]propylcarbamate

HRID 896619Notes

Reaction equation

HRID 896619 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][N:12]1[C:16]([C:17](OCC)=O)=[CH:15][S:14][C:13]1=[N:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][C:30]([F:33])([F:32])[F:31])=[CH:25][CH:24]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.CS(Cl)(=O)=O.[CH3:46][NH:47][CH2:48][C:49]1[CH:54]=[CH:53][C:52]([Cl:55])=[CH:51][CH:50]=1>O1CCCC1.O>[Cl:55][C:52]1[CH:53]=[CH:54][C:49]([CH2:48][N:47]([CH2:17][C:16]2[N:12]([CH2:11][CH2:10][CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:4])[CH3:3])[C:13](=[N:22][C:23]3[CH:24]=[CH:25][C:26]([O:29][C:30]([F:31])([F:33])[F:32])=[CH:27][CH:28]=3)[S:14][CH:15]=2)[CH3:46])=[CH:50][CH:51]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66905Benzenemethanamine, 4-chloro-N-methyl-HCID 22350979Ethyl 3-{3-[(tert-butoxycarbonyl)amino]propyl}-2-{[4-(trifluoromethoxy)phenyl]imino}-2,3-dihydrothiazol-4-carboxylate

Product 1

HCID 22350950tert-Butyl 3-[4-{[(4-chlorobenzyl)(methyl)amino]methyl}-2-{[4-(trifluoromethoxy)phenyl]imino}thiazol-3(2H)-yl]propylcarbamateYield 23.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The compound (300 mg) obtained in Example 208 (2) and triethylamine (101 mg) were dissolved in tetrahydrofuran (30 ml), and thereto was added dropwise methanesulfonyl chloride (115 mg) under ice-cooling. The mixture was stirred at the same temperature for 1.5 hour, and thereto was further added N-methyl-4-chlorobenzylamine (1.04 g), and the mixture was further stirred for one hour. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated brine, dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography [n-hexane:ethyl acetate (2:1)] to give the title compound (83 mg) as oil. (2)N-[3-(3-Aminopropyl)-4-{[(4-chlorobenzyl)(methyl)amino]methyl}thiazol-2(3H)-ylidene]-4-(trifluoromethoxy)aniline

Workup

  1. temperaturecooling
  2. stirringthe mixture was further stirred for one hour
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with a saturated brine
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography [n-hexane:ethyl acetate (2:1)]

Sources & evidence

ORD record
ord-399222bddedc44ecbdf3e0326330419b
Source dataset
uspto-grants-2005_07
Patent number
US06919361B2

Reaction notes

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