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

HRID 1930425ノート

反応式

HRID 1930425 の反応式
[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]

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-ea3609b9da9d42e6be50c8230bd75732
出典データセット
uspto-grants-2012_05
特許番号
US08188113B2

反応ノート

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