Triethylamine → (2R,4R)-2-[2-Fluoro-4-(3-methyl-pyrazol-1-yl)-phenylcarbamoyl]-4-methoxy-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 2217574노트

반응식

HRID 2217574 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][CH3:14])[CH2:10][C@@H:9]1[C:15]([OH:17])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:18][C:19]1[CH:24]=[C:23]([N:25]2[CH:29]=[CH:28][C:27]([CH3:30])=[N:26]2)[CH:22]=[CH:21][C:20]=1[NH2:31].CCOC1N(C(OCC)=O)C2C(=CC=CC=2)C=C1.CCN(CC)CC>C(Cl)(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][CH3:14])[CH2:10][C@@H:9]1[C:15](=[O:17])[NH:31][C:20]1[CH:21]=[CH:22][C:23]([N:25]2[CH:29]=[CH:28][C:27]([CH3:30])=[N:26]2)=[CH:24][C:19]=1[F:18])=[O:7])([CH3:2])([CH3:3])[CH3:4]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 11459222(2R,4R)-1-[(tert-butoxy)carbonyl]-4-methoxypyrrolidine-2-carboxylic acidHCID 221815262-Fluro-4-(3-methyl-pyrazol-1-yl)phenylamine

생성물 1

HCID 68805326(2R,4R)-2-[2-Fluoro-4-(3-methyl-pyrazol-1-yl)-phenylcarbamoyl]-4-methoxy-pyrrolidine-1-carboxylic acid tert-butyl ester

시약·촉매·용매 1

HCID 6212Chloroform용매2회

실험 절차

(2R,4R)-4-methoxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (0.350 g, 1.427 mmol), aniline 1 (0.273 g, 1.427 mmol) and EEDQ (0.529 g, 2.140 mmol) were dissolved in CHCl3 (30 mL). Et3N (0.6 mL, 4.281 mmol) was added and the reaction mixture was heated at reflux for 18 h. The mixture was allowed to cool and diluted with CHCl3 (100 mL) and washed with 5% HCl, 0.5 N NaOH, water and brine (40 mL each), the organic extract was dried over MgSO4, filtered and the solvent removed to give a pale tan foam. The crude product was used for the next step without purification. MS: APCI (AP+): 419.2 (M)+, (AP−): 417.2 (M)−.

후처리

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 18 h
  3. temperatureto cool
  4. washwashed with 5% HCl, 0.5 N NaOH, water and brine (40 mL each)
  5. extractionthe organic extract
  6. dry with materialwas dried over MgSO4
  7. filtrationfiltered
  8. customthe solvent removed
  9. customto give a pale tan foam
  10. customThe crude product was used for the next step without purification

출처 및 근거

ORD 기록
ord-aec5810b2ffe491ea8b9443d16fdcac4
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07407974B2

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