Water → Ethyl 3-(6-aminopyridin-3-yl)-2-[1-(2-oxo-1-phenylpyrrolidin-3-yl)-1H-imidazol-4-yl]-propionate

HRID 2370921노트

반응식

HRID 2370921 반응식
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH:9]([C:15]2[N:16]=[CH:17][NH:18][CH:19]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH:23]1[CH2:27][CH2:26][N:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:24]1=[O:34].O>CN(C=O)C>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH:9]([C:15]2[N:16]=[CH:17][N:18]([CH:23]3[CH2:27][CH2:26][N:25]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[C:24]3=[O:34])[CH:19]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 34652323-Bromo-1-phenylpyrrolidin-2-oneHCID 178470993HCID 178470993, 화합물

생성물 1

HCID 69330945Ethyl 3-(6-aminopyridin-3-yl)-2-[1-(2-oxo-1-phenylpyrrolidin-3-yl)-1H-imidazol-4-yl]-propionate수율 54.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 60.1 mg (0.23 mmol) of the compound from example 1g in 1 ml of absolute DMF was mixed with 11 mg (0.23 mmol) of sodium hydride (50%) and stirred at RT for 1 h. Then 55.5 mg (0.23 mmol) of (+/−)-3-bromo-1-phenyl-2-pyrrolidinone were added, and the mixture was stirred at RT for 45 min. The reaction solution was mixed with 1 ml of water and extracted several times with EA. The combined EA extracts were dried over Na2SO4, filtered and concentrated. Purification of the resulting residue by chromatography on silica gel with CH2Cl2/methanol (92:8 to 85:15 in 35 min) as mobile phase afforded 52.2 mg of the title compound.

후처리

  1. stirringthe mixture was stirred at RT for 45 min
  2. extractionextracted several times with EA
  3. dry with materialThe combined EA extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification of the resulting residue by chromatography on silica gel with CH2Cl2/methanol (92:8 to 85:15 in 35 min) as mobile phase

출처 및 근거

ORD 기록
ord-d3860a4c39ce4660be2d24dc02934a79
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08710232B2

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