Sodium Sulfate → Carbamic acid, [2-methyl-4-[[(2-methyl-4-pyridinyl)amino]carbonyl]-5-thiazolyl]-, 1,1-dimethylethyl ester

HRID 2244451ノート

反応式

HRID 2244451 の反応式
[CH3:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=1.C[Al](C)C.C([O:15][C:16]([C:18]1[N:19]=[C:20]([CH3:31])[S:21][C:22]=1[NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=O)C.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCOCC1.O>[C:27]([O:26][C:24](=[O:25])[NH:23][C:22]1[S:21][C:20]([CH3:31])=[N:19][C:18]=1[C:16](=[O:15])[NH:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([CH3:1])[CH:7]=1)([CH3:30])([CH3:28])[CH3:29]

参加物

7

反応物 4

HCID 24436Sodium SulfateHCID 7286704-Amino-2-methylpyridineHCID 16682925TrimethylaluminumHCID 68405841Ethyl 5-((tert-butoxycarbonyl)amino)-2-methylthiazole-4-carboxylate

生成物 1

HCID 68406749Carbamic acid, [2-methyl-4-[[(2-methyl-4-pyridinyl)amino]carbonyl]-5-thiazolyl]-, 1,1-dimethylethyl ester収率 83%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

A solution of 2-methyl-pyridin-4-ylamine (0.623 g, 5.77 mmol) in 20 ml dry dioxane was treated at 0° C. with trimethylaluminium (2M in hexane, 2.88 ml, 5.77 mmol). The mixture was stirred at room temperature for 1 h. 5-tert-Butoxycarbonylamino-2-methyl-thiazole-4-carboxylic acid ethyl ester (0.55 g, 1.92 mmol) was added and the reaction mixture was refluxed for 4 h. 1 ml water and 2 g sodium sulfate were sequentially added and filtered. The filtrate was evaporated and the residue purified by flash chromatography on silica gel with heptane/ethyl acetate 100:0→0:100 to yield [2-methyl-4-(2-methyl-pyridin-4-ylcarbamoyl)-thiazol-5-yl]-carbamic acid tert-butyl ester (0.555 g, 83%) as a light yellow solid, MS (ISP): m/e=349.5 (M+H+).

後処理

  1. temperaturethe reaction mixture was refluxed for 4 h
  2. filtrationfiltered
  3. customThe filtrate was evaporated
  4. customthe residue purified by flash chromatography on silica gel with heptane/ethyl acetate 100:0→0:100

出典と根拠

ORDレコード
ord-71d13187d31e41738a3cf48626588c9d
出典データセット
uspto-grants-2010_03
特許番号
US07678815B2

反応ノート

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