1,2-Dichloroethane → ethyl 3-tert-butyl-1-(2-morpholino-2-oxoethyl)-1H-pyrazole-5-carboxylate

HRID 1930425노트

반응식

HRID 1930425 반응식
[C:1]([C:5]1[CH:9]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:7]([CH2:15][C:16]([OH:18])=O)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[NH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1.Cl>CN(C=O)C.O>[C:1]([C:5]1[CH:9]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:7]([CH2:15][C:16]([N:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)=[O:18])[N:6]=1)([CH3:2])([CH3:3])[CH3:4]

참가 물질

8

반응물 5

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 8083MorpholineHCID 757711-HydroxybenzotriazoleHCID 206071732-(3-tert-butyl-5-(ethoxycarbonyl)-1H-pyrazol-1-yl)acetic acid

생성물 1

HCID 69036388ethyl 3-tert-butyl-1-(2-morpholino-2-oxoethyl)-1H-pyrazole-5-carboxylate수율 69%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2-(3-tert-butyl-5-(ethoxycarbonyl)-1H-pyrazol-1-yl)acetic acid from Example B17 (0.77 g, 3.02 mmol) in DMF (5 mL) were added EDC (0.75 g, 3.93 mmol), HOBt (0.55 g, 3.62 mmol) and morpholine (0.39 g, 4.53 mmol). After stirring the mixture for 4 h at RT, water (50 mL) and 3M HCl (5 mL) were added and the product was extracted with EtOAc (3×30 mL). The combined organic layers were washed with aq. LiCl, dried (Na2SO4), concentrated and purified by chromatography (EtOAc/CH2Cl2) to afford ethyl 3-tert-butyl-1-(2-morpholino-2-oxoethyl)-1H-pyrazole-5-carboxylate (0.67 g, 69% yield) as a solid. 1H NMR (400 MHz, Acetone-d6): δ 6.74 (s, 1H), 5.40 (s, 2H), 4.27 (q, J=7.2 Hz, 2H), 3.73 (brs, 2H), 3.65-3.62 (m, 4H), 3.51 (brs, 2H), 1.32 (t, J=7.2 Hz, 3H), 1.29 (s, 9H); MS (ESI) m/z: 324.2 (M+H+).

후처리

  1. extractionthe product was extracted with EtOAc (3×30 mL)
  2. washThe combined organic layers were washed with aq. LiCl
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified by chromatography (EtOAc/CH2Cl2)

출처 및 근거

ORD 기록
ord-ea3609b9da9d42e6be50c8230bd75732
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188113B2

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