Cyclohexanecarbonyl chloride → (2Z)-2-(3-butyl-4-methyl-1,3-thiazol-2(3H)-ylidene)-1-cyclohexylethanone

HRID 448030노트

반응식

HRID 448030 반응식
[I-].[CH2:2]([N+:6]1[C:10]([CH3:11])=[CH:9][S:8][C:7]=1[CH3:12])[CH2:3][CH2:4][CH3:5].[CH:13]1([C:19](Cl)=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1>C(Cl)Cl.CN(C1C=CN=CC=1)C.CS(C)=O.CO>[CH2:2]([N:6]1[C:10]([CH3:11])=[CH:9][S:8]/[C:7]/1=[CH:12]\[C:19]([CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:20])[CH2:3][CH2:4][CH3:5]

참가 물질

6

반응물 2

HCID 75938Cyclohexanecarbonyl chlorideHCID 691651093-Butyl-2,4-dimethylthiazol-3-ium iodide

생성물 1

HCID 24955354(2Z)-2-(3-butyl-4-methyl-1,3-thiazol-2(3H)-ylidene)-1-cyclohexylethanone

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매3회HCID 22036561Dimethyl sulfoxide methanol용매

실험 절차

In a 20 mL vial a solution of 3-butyl-2,4-dimethylthiazol-3-ium iodide (47.92 mg, 0.16 mmol) dissolved in CH2Cl2 (0.5 mL) was added, followed by the addition of DMAP (49.24 mg, 0.40 mmol) dissolved in CH2Cl2 (0.8 mL). Then, to the solution was added cyclohexanecarbonyl chloride (23.5 mg, 0.16 mmol) dissolved in CH2Cl2 (0.5 mL). The vial was capped and shaken overnight at room temperature. The residue was dissolved in 1:1 DMSO/MeOH and purified by reverse phase HPLC using a method analogous to that described in Example 53 to provide the title compound. 1H NMR (500 MHz, DMSO-d6/D2O) δ ppm 0.92 (t, 3 H) 1.09-1.44 (m, 7 H) 1.51-1.70 (m, 3 H) 1.69-1.88 (m, 4 H) 2.21-2.36 (m, 4 H) 3.95-4.01 (m, 2 H) 5.79-5.91 (m, 1 H) 6.57-6.73 (m, 1 H) MS (ESI) positive ion 280 (M+H).

후처리

  1. additionwas added
  2. customThe vial was capped
  3. custompurified by reverse phase HPLC

출처 및 근거

ORD 기록
ord-6723b46411c84ee8a8b22065c6f55ab3
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481574B2

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