Diisopropylethylamine → 1-(3-(3,4-dimethoxyphenyl)-1H-pyrazol-1-yl)-2-methoxy-2-(4-morpholinophenyl)ethanone

HRID 1798646노트

반응식

HRID 1798646 반응식
[CH3:1][O:2][CH:3]([C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:9][CH:8]=1)[C:4]([OH:6])=O.[CH3:19][O:20][C:21]1[CH:22]=[C:23]([C:29]2[CH:33]=[CH:32][NH:31][N:30]=2)[CH:24]=[CH:25][C:26]=1[O:27][CH3:28].C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.C([O-])(O)=O.[Na+]>CN(C=O)C>[CH3:19][O:20][C:21]1[CH:22]=[C:23]([C:29]2[CH:33]=[CH:32][N:31]([C:4](=[O:6])[CH:3]([O:2][CH3:1])[C:7]3[CH:12]=[CH:11][C:10]([N:13]4[CH2:18][CH2:17][O:16][CH2:15][CH2:14]4)=[CH:9][CH:8]=3)[N:30]=2)[CH:24]=[CH:25][C:26]=1[O:27][CH3:28]

참가 물질

7

반응물 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2733179PyBroPHCID 584321092-Methoxy-2-(4-morpholinophenyl)acetic acidHCID 178488676HCID 178488676, 화합물

생성물 1

HCID 584320151-(3-(3,4-dimethoxyphenyl)-1H-pyrazol-1-yl)-2-methoxy-2-(4-morpholinophenyl)ethanone수율 489.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2-methoxy-2-(4-morpholinophenyl)acetic acid (0.1 g, 0.42 mmol) and 3-(3,4-dimethoxyphenyl)-1H-pyrazole (0.86 g, 0.42 mmol) in anhydrous DMF (4 mL) at room temperature was added diisopropylethylamine (0.22 ml, 1.26 mmol) then bromotripyrrolidinophosphonium hexafluorophosphate (0.23 g, 0.50 mmol). After 24 hrs, saturated aqueous NaHCO3 was added. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organics were washed with H2O and brine, dried over Na2SO4 and concentrated in vacuo. Purification by chromatography (0-60% EtOAc-hexanes) gave 1-(3-(3,4-dimethoxyphenyl)-1H-pyrazol-1-yl)-2-methoxy-2-(4-morpholinophenyl)ethanone as a white solid (0.90 g, 50% yield). MS: m/z 438.2 [M+H]+.

후처리

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with EtOAc
  3. washThe combined organics were washed with H2O and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customPurification by chromatography (0-60% EtOAc-hexanes)

출처 및 근거

ORD 기록
ord-6ad9b28371af492d9f70aa09c19bbb5a
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08343970B2

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