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

HRID 2244446

반응식

HRID 2244446 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-3a8640564c8f4d2193d61c94b1387a8f
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07678815B2

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