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

HRID 2370921ノート

反応式

HRID 2370921 の反応式
[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

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 34652323-Bromo-1-phenylpyrrolidin-2-oneHCID 178470993HCID 178470993、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d3860a4c39ce4660be2d24dc02934a79
出典データセット
uspto-grants-2014_04
特許番号
US08710232B2

反応ノート

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