Diisopropylethylamine → tert-Butyl 4-{4-[ethyl(1-methyl-2-oxo-2-phenylethyl)carbamoyl]thiazol-2-yl}-piperidine-1-carboxylate

HRID 2243106노트

반응식

HRID 2243106 반응식
[C:1]([C:4]1[N:5]=[C:6]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[S:7][CH:8]=1)([OH:3])=O.Cl.[CH2:23]([NH:25][CH:26]([CH3:35])[C:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:28])[CH3:24].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)C(C)C)C>CN(C)C=O>[CH2:23]([N:25]([CH:26]([CH3:35])[C:27](=[O:28])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:1]([C:4]1[N:5]=[C:6]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[S:7][CH:8]=1)=[O:3])[CH3:24]

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 458518Ethcathinone hydrochlorideHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27955312-(1-((Tert-butoxy)carbonyl)piperidin-4-yl)-1,3-thiazole-4-carboxylic acid

생성물 1

HCID 3849190tert-Butyl 4-{4-[ethyl(1-methyl-2-oxo-2-phenylethyl)carbamoyl]thiazol-2-yl}-piperidine-1-carboxylate수율 85%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

tert-Butyl 4-(4-carboxythiazol-2-yl)piperidine-1-carboxylate (6.5 mmol; 2.03 g) is dissolved in 40 ml of anhydrous dimethylformamide and placed under an inert atmosphere, and 2-(ethylamino)propiophenone hydrochloride (1 eq.; 6.5 mmol; 1.39 g), HBTU (1 eq.; 6.5 mmol; 2.47 g) and N-ethyldiisopropylamine (3.5 eq.; 22.75 mmol; 3.97 ml) are then added. The reaction medium is stirred at room temperature overnight. The reaction medium is evaporated to dryness and then taken up in dichloromethane and washed with saturated potassium carbonate (K2CO3) solution, citric acid solution and water (twice). The organic phase is dried over sodium sulfate and then evaporated to dryness. The crude product is chromatographed on silica, using a 1/1 ethyl acetate/hexane mixture as eluent (Rf=0.55) to give 2.6 g of expected product in the form of an oil.

후처리

  1. additionare then added
  2. customThe reaction medium is evaporated to dryness
  3. washwashed with saturated potassium carbonate (K2CO3) solution, citric acid solution and water (twice)
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customevaporated to dryness
  6. customThe crude product is chromatographed on silica

출처 및 근거

ORD 기록
ord-88011d5b2361485eaeff9f6c485d2974
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07674803B2

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