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

HRID 896619ノート

反応式

HRID 896619 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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

後処理

  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)]

出典と根拠

ORDレコード
ord-399222bddedc44ecbdf3e0326330419b
出典データセット
uspto-grants-2005_07
特許番号
US06919361B2

反応ノート

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